Urea derivatives and their use as acat inhibitors

Abstract: Urea derivatives of formula (I) wherein the valuable groups are as defined in the specification, which possess both an ACAT inhibitory activity and an antioxidative activity. Those derivatives are useful in the prophylaxis and treatment of hypercholesterolemia and atherosclerosis.

Description: FIELD OF THE INVENTION This invention relates to new urea derivatives, processes for their preparation and their use in medicine. More particularly, the invention relates to compounds having an inhibitory activity against an acyl coenzyme A cholesterol acyltransferase (called hereafter ACAT) and having a protective ability against an oxidative modification of low density lipoprotein (called hereafter LDL). BACKGROUND OF THE INVENTION In recent years, interest has been directed to the relationship between increase in the level of cholesterol in the serum and human health. It has been pointed out that the level of cholesterol in the serum is associated with the amount of cholesterol deposited in the blood vessel system and the deposition of cholesterol in the blood vessel system brings about e.g. coronary artery lesion, which is responsible for ischemic heart disease. Drugs for reducing the level of cholesterol in the serum have been developed. These drugs, however, were effective in controlling blood cholesterol to an appropriate level, but ineffective in inhibiting absorption of cholesterol from the digestive tracts and deposition of cholesterol on the wall of blood vessels. ACAT is an enzyme that catalyzes the synthesis of cholesteryl esters from acyl coenzyme A and cholesterol and plays an important role in cholesterol metabolism and its absorption from the digestive tracts. It is believed that ACAT occurs in the site of mucosa cells of intestinal tracts and is active in esterification and incorporation of cholesterol derived from the diet. On the other hand, the cholesterol deposited on the wall of blood vessels is the esterified cholesterol. The cholesterol accumulated in the foam cells which plays in important role in the formation of atherosclerosis lesion is also esterified cholesterol. The enzyme that catalyzes the esterification of cholesterol in these sites is also ACAT. Accordingly, the inhibition of ACAT activity can result in inhibiting the incorporation in vivo of cholesterol derived from the diet and further the formation of cholesteryl ester in specified cell sites. Compounds having an ACAT inhibitory activity are disclosed in EP 0450660 A1 and EP 0477778 A2. However, those known compounds have only an ACAT inhibitory activity and give no effect on the oxidative modification of LDL causing the foam cell transformation of macrophage which is an important phenomenon for the formation of atherosclerosis lesion. The foam cells which play an important role in the formation of atherosclerosis lesion are products of uptake of oxidatively modified LDL into macrophage which results in the foam cell transformation of the macrophage. It is reported by Diane W. Morel et al. (Atheroma, Vol. 4, pages 357-364, 1984) that, the oxidatively modified LDL causes foam cell transformation of macrophage and plays an important role in the formation of atherosclerosis lesion. A report of TORU KITA et al. (Proc. Natl. Acad. Sci. USA, Vol. 84, pages 5928-5931, 1987) demonstrates that prevention of the oxidative modification of LDL induces regression of the atherosclerosis lesion. Therefore, inhibition of the oxidative modification of LDL, in addition to the above-mentioned ACAT inhibitory activity, is very important in preventing the formation and progression as well as inducing regression of atherosclerosis lesion. Under such circumstances, it has been desired to develop compounds having an ACAT inhibitory activity and capable of inhibiting an oxidative modification of LDL or the like, since such compounds may decrease the serum cholesterol level and inhibit the oxidative modification of LDL cholesterol deposited on the blood vessel or tissue, thus being effective for inhibiting the formation and progression of atherosclerosis lesions and inducing its regression. EP-A-0 527 458 discloses certain new 3,5-di-tert-butyl-4-hydroxyphenyl derivatives which are described as having antioxidant activity and being capable of inhibiting ACAT-dependent esterification. The compounds disclosed are described as being useful as medicaments, especially as anti-atherosclerotics. DETAILED DESCRIPTION OF THE INVENTION We have now found new urea derivatives which exhibit both an ACAT inhibitory activity and an antioxidative activity. The urea derivatives of the present invention possess an ACAT inhibitory activity, thereby inhibiting absorption of cholesterol from the intestinal tracts, lowering blood cholesterol level and inhibiting accumulation of cholesteryl esters in the wall of blood vessels, atheroma and macrophage, and simultaneously an antioxidative activity i.e. a protective activity against the oxidative modification of LDL which participates in foam cell transformation of macrophage thereby effectively inhibiting the formation and progression of atherosclerosis lesion and inducing its regression. According to one aspect of the present invention, there is provided a compound of formula (I) and pharmaceutically acceptable salts thereof, which exhibits both an ACAT inhibitory activity and an antioxidative activity. in which: R 1 and R 2 , which may be the same or different, each represents a hydrogen atom, a halogen atom, a straight or branched (C 1 -C 6 )alkyl group or a straight or branched (C 1 -C 6 )alkoxy group, R 3 and R 4 , which may be the same or different, each represents a hydrogen atom, a straight or branched (C 1 -C 12 )alkyl group, a straight or branched (C 2 -C 20 )alkenyl group, a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxycarbonyl(C 1 -C 9 )alkyl group, a benzyloxycarbonyl(C 1 -C 6 )alkyl group in which the alkyl moiety is optionally substituted by phenyl, a N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkyl group, a N-(C 1 -C 6 )alkyl-N-benzylamino(C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkylthio(C 1 -C 6 )alkyl group, an oxo(C 1 -C 9 )alkyl group, a hydroxy(C 1 -C 6 )alkyl group, a dihydroxy(C 1 -C 6 )alkyl group, a cyclo(C 3 -C 15 )alkyl group, a cyclo(C 3 -C 8 )alkyl(C 1 -C 6 )alkyl group, a dicyclo(C 3 -C 9 )alkyl(C 1 -C 6 )alkyl group, a bicyclo(C 6 -C 9 )alkyl group, a tricyclo(C 9 -C 12 )alkyl group, in which in all cases the cycloalkyl group or the cycloalkyl moiety is optionally substituted by one or two substituents selected from the group consisting of (C 1 -C 6 )alkyl, hydroxy, amino, acetoxy, acetamido, phenyl, benzyloxy, dimethylaminophenyl, and methylenedioxyphenyl, which may be further fused with a benzene ring, an aryl group, an aryl(C 1 -C 6 )alkyl group, a diaryl(C 1 -C 6 )alkyl group, in which in all cases the aryl group or the aryl moiety is optionally substituted by one, two or three substituents selected from the group consisting of (C 1 -C 6 )alkyl, (C 1 -C 6 )alkyloxy, halogen, nitro, hydroxy, amino, dimethylamino, methylenedioxy, and pyrrolidinyl, a heterocyclic group or a heterocyclic group attached to a (C 1 -C 6 )alkylene chain, in which in all cases the heterocyclic group represents a saturated or unsaturated, 5 to 8 membered ring monocyclic or bicyclic, heterocyclic group containing 1 to 3 heteroatoms selected from the group consisting of S, O and N, and the heterocyclic group is optionally substituted by one or two substituents selected from the group consisting of acetyl, hydroxy, (C 1 -C 9 )alkyl, (C 1 -C 9 )alkyloxy, cyclo(C 3 -C 8 )alkyl, cyclo(C 3 -C 8 )alkyl(C 3 -C 10 )alkyl, pyridyl(C 1 -C 6 )alkyl, phenyl, phenyl(C 1 -C 6 )alkyl, diphenyl(C 1 -C 6 )alkyl, and phenylpiperazinyl, the phenyl group or the phenyl moiety being optionally substituted by one or two substituents selected from the group consisting of halogen, hydroxy, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, cyano, diethylamino and trifluoromethyl, which may be further fused with a benzene ring, and further R 3 and R 4 , together with the nitrogen atom to which they are attached, may form a saturated or unsaturated heterocyclic group, in which the heterocyclic group represents a 5 to 8 membered ring monocyclic or bicyclic, heterocyclic group or a group derived from a heterocyclic spiro compound, which may contain one or two heteroatoms selected from the group consisting of S, O or N, the heterocyclic group being optionally substituted by one or two substituents selected from the group consisting of (C 1 -C 6 )alkyl, hydroxy, hydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl, acetoxy(C 1 -C 6 )alkyl, (C 1 -C 9 )alkylcarbonyl, (C 1 -C 6 )alkoxycarbonyl, amino, tosyl, phenyl, halogenophenyl, (C 1 -C 6 )alkoxyphenyl, phenyl(C 1 -C 6 )alkyl, benzyloxy, benzyloxy(C 1 -C 6 )alkyl, tolyl, xylyl, benzoyl, methylenedioxyphenyl(C 1 -C 6 )alkyl, pyridyl, pyridylcarbonyl, piperidyl, pyrrolidinyl(C 1 -C 6 )alkyl and pyrrolidinylcarbonyl(C 1 -C 6 )alkyl, which may be further fused with a benzene ring, in which in all cases the alkyl and alkoxy moieties may be either straight or branched, with the proviso that both R 3 and R 4 do not represent a hydrogen atom at the same time; R 5 and R 6 , which may be the same or different, each represents a straight or branched (C 1 -C 6 )alkyl group; and the line represents -CH 2 CH 2 - or -CH=CH-. Referring to R 1 and R 2 in formula (I), the halogen atom includes fluorine, chlorine, bromine and iodine, the (C 1 -C 6 )alkoxy group includes e.g. methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy and hexyloxy, and the (C 1 -C 6 )alkyl group includes e.g. methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl and hexyl. Referring to R 3 and R 4 in formula (I), the (C 1 -C 12 )alkyl group includes e.g. methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl, isohexyl, heptyl, octyl, trimethylpentyl, 2,4,4-trimethyl-2-pentyl, nonyl, decyl and dodecyl. The (C 2 -C 20 )alkenyl group includes e.g. vinyl, allyl, isopropenyl, 2-butenyl, 2-pentenyl, 4-pentenyl, 3-hexenyl, 5-hexenyl, 4-octenyl, 7-octenyl, 7-decenyl, 3,7-dimethyl-2,6-octadienyl, 10-tetradecenyl, 8-heptadecenyl, 8-octadecenyl and 4,7,10,13,16-nonadecapentaenyl. The (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group includes e.g. 2-methoxyethyl, 4-methoxybutyl, 2-methoxybutyl, 6-methoxyhexyl, ethoxymethyl, 3-ethoxypropyl, 2-propoxyethyl, 5-propoxypentyl, isopropoxymethyl, butoxymethyl, 2-isobutoxyethyl, sec-butoxymethyl, tert-butoxymethyl, pentyloxymethyl, 2-pentyloxyethyl and hexyloxymethyl. The (C 1 -C 6 )alkoxycarbonyl(C 1 -C 9 )alkyl group includes e.g. 2-(methoxycarbonyl)ethyl, 7-(methoxycarbonyl)heptyl, 2-(ethoxycarbonyl)ethyl, 4-(ethoxycarbonyl)butyl, propoxycarbonylmethyl, 3-(propoxycarbonyl)butyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, 1-(butoxycarbonyl)ethyl, 2-(isobutoxycarbonyl)ethyl, sec-butoxycarbonylmethyl, 2-(tert-butoxycarbonyl)ethyl, pentyloxycarbonylmethyl and 2-(hexyloxycarbonyl)ethyl, α-(methoxycarbonyl)benzyl, α-(ethoxycarbonyl)benzyl. The benzyloxycarbonyl(C 1 -C 6 )alkyl group includes benzyloxycarbonylmethyl, 2-(benzyloxycarbonyl)ethyl, 6-(benzyloxycarbonyl)hexyl, 4-(benzyloxycarbonyl)butyl and α-(benzyloxycarbonyl)benzyl. The N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkyl group includes e.g. 2-(N,N-dimethylamino)ethyl, 4-(N,N-dimethylamino)butyl, 2-(N,N-diethylamino)ethyl, 3-(N,N-diethylamino)propyl, N,N-diisopropylaminomethyl, N,N-dibutylaminomethyl, 2-(N,N-dibutylamino)ethyl, 2-(N,N-diisobutylamino)ethyl, N,N-dipentylaminomethyl, 2-(N,N-dihexylamino)ethyl and N,N-diisohexylaminomethyl. The N-(C 1 -C 6 )alkyl-N-benzylamino(C 1 -C 6 )alkyl includes e.g. 2-(N-benzyl-N-methylamino)ethyl, 2-(N-benzyl-N-ethylamino)ethyl, 4-(N-benzyl-N-methylamino)butyl, 2-(N-benzyl-N-ethylamino)ethyl and 3-(N-benzyl-N-ethylamino)propyl. The (C 1 -C 6 )alkylthio(C 1 -C 6 )alkyl group includes e.g. 2-(methylthio)ethyl, 2-(ethylthio)ethyl, propylthiomethyl, 2-(isopropylthio)ethyl, 1-(butylthio)ethyl, isobutylthiomethyl, tert-butylthiomethyl, pentylthiomethyl and hexylthiomethyl. The oxo(C 1 -C 9 )alkyl group includes e.g. 2-oxopropyl, 2-oxobutyl, 4-oxopentyl, 6-oxoheptyl and 2-oxooctyl. The hydroxy(C 1 -C 6 )alkyl group includes e.g. 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 3-hydroxybutyl and 6-hydroxyhexyl. The dihydroxy(C 1 -C 6 )alkyl group includes e.g. 2,3-dihydroxypropyl, 4,5-dihydroxypentyl, 1,5-dihydroxy-3-pentyl, 2-ethyl-1,3-dihydroxy-2-propyl, and 2,4-dihydroxy-3-methylpentyl. The cyclo(C 3 -C 15 )alkyl group includes e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, cyclododecyl, 1-phenylcyclopentyl, 4-(benzyloxy)cyclohexyl, 4-aminocyclohexyl, 4-acetamidocyclohexyl, 4-hydroxycyclohexyl, 4-acetoxycyclohexyl, 4-tert-butylcyclohexyl, 2,3-dimethylcyclohexyl, 1,2,3,4-tetrahydronaphthyl, cyclododecyl and benzyloxycyclohexyl. The cyclo(C 3 -C 8 )alkyl(C 1 -C 8 )alkyl group includes e.g. cyclopropylmethyl, 2-cyclobutylethyl, 2-cycloheptylethyl, cyclohexylmethyl, 3-cyclohexylpropyl, 4-cyclohexylbutyl, cyclooctylmethyl, 5-cyclooctylpentyl, 1-(4-dimethylaminophenyl)cyclopentylmethyl and 1-(3,4-methylenedioxyphenyl)cyclopentylmethyl. The dicyclo(C 3 -C 9 )alkyl(C 1 -C 6 )alkyl group includes e.g. dicyclohexylmethyl, 2,2-dicyclohexylethyl and 3,3-dicyclohexylpropyl. The bicyclo(C 6 -C 9 )alkyl group includes e.g. bicyclo[3.3.0]-2-octyl, bicyclo[3.3.1]-2-nonyl and bicyclo[3.2.1]-2-octyl. The tricyclo(C 9 -C 12 )alkyl group includes e.g. tricyclo[5.2.1.0 2.6 ]decyl and tricyclo[3.3.1.1 3.7 ]decyl. The aryl group includes e.g. phenyl, 1-naphthyl, 2-naphthyl, 3-naphthyl, 4-methylphenyl, 2,6-diisopropylphenyl, 3,5-di-tert-butyl-4-hydroxyphenyl, 2-methoxyphenyl, 4-hexyloxyphenyl, 4-fluorophenyl, 2-nitrophenyl, 4-chloronaphthyl, 3-amino-2-naphthyl, 5-hydroxynaphthyl, 5-methoxynaphthyl and anthryl. The aryl(C 1 -C 6 )alkyl group includes e.g. benzyl, phenethyl, α-methylbenzyl, 3-phenylpropyl, 4-phenylbutyl, 9-anthrylmethyl, 4-ethylbenzyl, 4-ethoxybenzyl, 4-fluorobenzyl, 3,4-methylenedioxybenzyl, 3,4,5-trimethoxybenzyl, 4-methylphenethyl, 2-methoxyphenethyl, 4-methoxyphenethyl, 3,4-dimethoxyphenethyl, 3-chlorophenethyl, 4-chlorophenethyl, 4-fluorophenethyl, 4-nitrophenethyl, 3,4,5-trimethoxyphenethyl, 4-nitrophenylbutyl, 1-(4-fluorophenyl)-2-methylpropyl, 3-(3,4-dichlorophenyl)propyl, 4-dimethylaminophenethyl, 2-(3,4-dichlorophenyl)-2-propyl, 2-(3,4-dichlorophenyl)-2-methylpropyl, 2-(2-fluorophenyl)-2-methylpropyl, 2-(3-fluorophenyl)-2-methylpropyl, 2-(4-fluorophenyl)-2-methylpropyl and 2-[4-(1-pyrrolidinyl)phenyl]-2-methylpropyl. The diaryl(C 1 -C 6 )alkyl group includes e.g. diphenylmethyl, 1,2-diphenylethyl, 2,2-diphenylethyl, 4,4-diphenylbutyl and 6,6-diphenylhexyl. The monocyclic, heterocyclic group includes e.g. 3-furyl, 2-thienyl, 3-pyrrolyl, 2-pyrrolidinyl, 2H-pyran-3-yl, 2-pyridyl, 4-piperidyl, 3-morpholinyl, 2-piperazinyl, 1-methyl-4-piperidyl, 1-benzyl-4-piperidyl, 1-methyl-3-piperidyl, 1-(2,4-difluorobenzyl)-4-piperidyl, 1-(3,4-difluorobenzyl)-4-piperidyl, 1-(3,5-difluorobenzyl)-4-piperidyl, 1-[2,4-bis(trifluoromethyl)benzyl]-4-piperidyl, 1-(4-methoxybenzyl)-4-piperidyl, 1-phenethyl-4-piperidyl, 1-(2-fluorobenzyl)-4-piperidyl, 1-(3-fluorobenzyl)-4-piperidyl, 1-(4-fluorobenzyl)-4-piperidyl, 1-(4-chlorobenzyl)-4-piperidyl, 1-(4-cyanobenzyl)-4-piperidyl, 1-(2-pyridylmethyl)-4-piperidyl, 1-(3-pyridylmethyl)-4-piperidyl, 1-(4-pyridylmethyl)-4-piperidyl, 1-[4-(N,N-diethylamino)benzyl]-4-piperidyl, 1-[bis(4-fluorophenyl)methyl]-4-piperidyl, 1-(4-fluorophenethyl)-4-piperidyl, 1-(2,4-dimethylbenzyl)-4-piperidyl, 1-acetyl-4-piperidyl, 1-(4-hydroxybenzyl)-4-piperidyl, 1-(3,4-dihydroxybenzyl)-4-piperidyl, 1-ethyl-4-piperidyl, 1-neopentyl-4-piperidyl, 1-cyclohexyl-4-piperidyl, 1-heptyl-4-piperidyl, 1-(2-propyl)-4-piperidyl, 1-benzyl-3-piperidyl, 2-phenyl-3-piperidyl, 1-cyclohexylmethyl-3-piperidyl, 1-benzyl-3-pyrrolidinyl, 2-methoxy-5-pyridyl, 2-(4-phenyl-1-piperazinyl)-5-pyridyl and 5,6-dimethyl-1,2,4-triazin-3-yl. The bicyclic, heterocyclic group includes e.g. 3-indolyl, 5-indazolyl, 2-quinolyl, 5-isoquinolyl, 2,4-dimethyl-1,8-naphthyridin-7-yl, 3,9-dimethyl-3,9-diazabicyclo[3.3.1]-7-nonyl, 9-methyl-3-oxa-9-azabicyclo[3.3.1]-7-nonyl, 9-(4-fluorobenzyl)-3-oxa-9-azabicyclo[3.3.1]-7-nonyl, 9-methyl-3-thia-9-azabicyclo[3.3.1]-7-nonyl, 8-methyl-8-azabicyclo[3.2.1]-3-octyl and 1-azabicyclo[2.2.2]-3-octyl. The heterocyclic group attached to an alkylene chain may be the above-mentioned monocyclic or bicyclic heterocyclic group attached to an alkylene chain, which includes e.g. 3-furylmethyl, 3-(2-thienyl)propyl, 2-(3-indolyl)ethyl, 2-(3-pyrrolyl)ethyl, 2-pyrrolidinylmethyl, 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl, 2-(2-pyridyl)ethyl, 2-(4-piperidyl)ethyl, 3-(3-morpholinyl)propyl, 3-indolylmethyl, 2-(5-indazolyl)ethyl, 2-quinolylmethyl, 3-(1-imidazolyl)propyl, 2-morpholinoethyl, 3-morpholinopropyl, 3-(2-methylpiperidyl)propyl, 2-(1-pyrrolidinyl)ethyl, [4-(4-fluorobenzyl)-3-morpholinyl]methyl and (1-benzyl-4-hydroxy-4-piperidyl)methyl. When R 3 and R 4 in formula (I), together with the nitrogen atom to which they are attached form the heterocyclic ring, the monocyclic, heterocyclic group includes e.g. pyrrolidinyl, 2,5-dimethyl-1-pyrrolidinyl, 3-hydroxy-1-pyrrolidinyl, 2-hydroxymethyl-1-pyrrolidinyl, 2-hydroxyethyl-1-pyrrolidinyl, 2-methoxymethyl-1-pyrrolidinyl, 2-(1-pyrrolidinylmethyl)pyrrolidinyl, 3-pyrrolin-1-yl, 2,5-dimethyl-3-pyrrolin-1-yl, piperidino, 2-methylpiperidino, 2-ethylpiperidino, 3-methylpiperidino, 4-methylpiperidino, 4-piperidinopiperidino, 3,3-dimethylpiperidino, 2,6-dimethylpiperidino, 3,5-dimethylpiperidino, 2,4-dimethylpiperidino, 2-(hydroxymethyl)piperidino, 2-(2-hydroxyethyl)piperidino, 2-(2-acetoxyethyl)piperidino, 3-hydroxypiperidino, 4-hydroxypiperidino, 4-oxopiperidino, 4-aminopiperidino, 4-benzylpiperidino, 2-[2-(benzyloxy)ethyl]piperidino, 3-(benzyloxy)piperidino, 1,2,3,6-tetrahydropyridyl, perhydroazepinyl, perhydroazocinyl, piperazinyl, 4-methyl-1-piperazinyl, 3-methyl-1-piperazinyl, 3,5-dimethyl-1-piperazinyl, 2,5-dimethyl-1-piperazinyl, 4-(2-hydroxyethyl)-1-piperazinyl, 4-pentanoyl-1-piperazinyl, 4-acetyl-1-piperazinyl, 4-p-toluenesulfonyl-1-piperazinyl, 4-benzyl-1-piperazinyl, 4-(3,4-methylenedioxybenzyl)-1-piperazinyl, 4-(2-pyridyl)-1-piperazinyl, 4-nicotinoyl-1-piperazinyl, 4-(1-pyrrolidinylcarbonylmethyl)-1-piperazinyl, 4-benzyl-1-piperidyl, 4-phenyl-1-piperidyl, 4-phenyl-1,2,3,6-tetrahydropyridyl, 4-phenyl-1-piperazinyl, 4-benzyl-1-piperazinyl, 4-(o-tolyl)-1-piperazinyl, 4-(2-fluorophenyl)-1-piperazinyl, 4-(2,3-xylyl)-1-piperazinyl, 4-(2-chlorophenyl)-1-piperazinyl, 4-(2-methoxyphenyl)-1-piperazinyl, 4-(2-ethoxyphenyl)-1-piperazinyl, 4-(m-tolyl)-1-piperazinyl, 4-(3,4-difluorophenyl)-1-piperazinyl, 4-(4-chlorophenyl)-1-piperazinyl, 4-(3,4-dimethoxyphenyl)-1-piperazinyl, homopiperazinyl, morpholino, 2,6-dimethylmorpholino, thiazolidinyl, thiomorpholino, pyrrolyl, 2-ethyl-1-pyrrolyl, 2,5-dimethyl-1-pyrrolyl, pyrazolyl, 3-methyl-1-pyrazolyl, 4-methyl-1-pyrazolyl, imidazolyl, 4-methyl-1-imidazolyl, 4-phenyl-1-imidazolyl, 1H-1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl, imidazolidinyl, 2-imidazolin-1-yl, pyrazolidinyl and 2-pyrazolin-1-yl. The bicyclic, heterocyclic group includes e.g. 4,5,6,7-tetrahydroindol-1-yl, 1,5,6,7-tetrahydro-4-oxoindol-1-yl, indolinyl, isoindolinyl, perhydroindol-1-yl, decahydroquinolinyl, perhydroisoquinolin-2-yl, 1,2,3,4-tetrahydrocarbazol-1-yl, 1,2,3,4-tetrahydroquinolin-1-yl, 1,2,3,4-tetrahydroisoquinolin-1-yl, 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl, 5H-dibenz[b,f]azepin-5-yl, 10,11-dihydro-5H-dibenz[b,f]azepin-5-yl, 3-azabicyclo[3.2.2]nonan-3-yl, 3-methyl-3,9-diazabicyclo[3.3.1]nonan-9-yl, 3-oxa-9-azabicyclo[3.3.1]nonan-9-yl and 3-thia-9-azabicyclo[3.3.1]nonan-9-yl. The group derived from the heterocyclic spiro compound includes e.g. 1,4-dioxa-8-azaspiro[4.5]-decan-8-yl, 1,4-dioxa-7-azaspiro[4.4]decan-7-yl, 1,5-dithia-9-azaspiro[5.5]undecan-9-yl and 1-phenyl-4-oxo-1,3,8-triazaspiro[4.5]decan-8-yl. It should be understood that the compounds of formula (I) include all of their possible isomers including stereoisomer, metabolite, metabolic precursor and metabolic intermediate. The compounds of formula (I) can be prepared by various conventional procedures as described below. The compounds of formula (I) are prepared by reacting a compound of formula (II) wherein R 1 and R 2 as well as R 5 and R 6 are as defined above, and denotes -CH 2 -CH 2 - or -CH=CH- with an isocyanate of formula (III) R-NCO wherein R denotes R 3 or R 4 , and R 3 and R 4 are as defined above in an organic solvent under ice-cooling or at a temperature up to room temperature. This reaction is performed using the compound of formula (III) in an amount of 0.1 to 10 moles, preferably 0.5 to 2 moles per mole of the compound of formula (II). Alternatively, the compounds of formula (I) are prepared by reacting an isocyanate of formula (IV) wherein R 1 and R 2 as well as R 5 and R 6 are as defined above, and denotes -CH 2 -CH 2 - or -CH=CH- with an amine of formula (V) wherein R denotes R 3 or R 4 , and R 3 and R 4 are as defined above in an organic solvent under ice-cooling or at a temperature up to room temperature. This reaction is performed using the compound of formula (V) in an amount of 0.1 to 10 moles, preferably 0.5 to 2 moles per mole of the compound of formula (IV). Alternatively, the compounds of formula (I) are prepared by reacting a carbamate of formula (VI) wherein R 1 and R 2 as well as R 5 and R 6 are as defined above, and denotes -CH 2 -CH 2 - or -CH=CH- with an amine of formula (V) wherein R denotes R 3 or R 4 , and R 3 and R 4 are as defined above in an organic solvent while heating at 50-150°C. This reaction is performed using the compound of formula (V) in an amount of 0.1 to 10 moles, preferably 0.5 to 2 moles per mole of the compound of formula (VI). Alternatively, the compounds of formula (I) are prepared by reacting a compound of formula (II) with a carbamate of formula (VII) wherein R denotes R 3 or R 4 , and R 3 and R 4 are as defined above in an organic solvent while heating to 50-150°C. This reaction is performed using the compound of formula (VII) in an amount of 0.1 to 10 moles, preferably 0.5 to 2 moles per mole of the compound of formula (II). The isocyanates of formula (III) or (IV) are prepared, for example, by treating a carboxylic acid of formula RCOOH wherein R denotes R 3 or R 4 , and R 3 and R 4 are as defined above or a derivative thereof with 1 to 10 moles, preferably 1 to 3 moles of diphenylphosphoryl azide, trimethylsilylazide or the like, per mole of the carboxylic acid, in an organic solvent to give an acyl azide, which is in turn subjected to a rearrangement reaction under heating at 50-150°C, or alternatively by reacting a compound of formula (V) or (II) with phosgen. The carbamate of formula (VI) or (VII) are prepared by reacting a compound of formula (II) or (V) with 0.1 to 10 moles, preferably 0.5 to 2 moles of phenyl chloroformate per mole of the compound in an organic solvent under ice-cooling or at a temperature up to room temperature. This reaction may be conducted in the presence of an acid binder. The acid binders include e.g. inorganic basic substances such as sodium hydride, potassium hydroxide, sodium carbonate, potassium carbonate and organic basic substances including secondary amines such as diisopropylamine and tertiary amines such as triethylamine, methylmorpholine, pyridine. The organic solvents used in each of the above-described reactions include aliphatic hydrocarbon solvents such as hexane, petroleum ether and cyclohexane, aromatic hydrocarbon solvents such as benzene, toluene and xylenes, halogenated hydrocarbon solvents such as methylene chloride, chloroform, carbon tetrachloride and dichloroethane, ether solvents such as ethyl ether, isopropyl ether, tetrahydrofuran and dioxane, ketone solvents such as acetone and methyl ethyl ketone, ethyl acetate, acetonitrile and N,N-dimethylformamide. The process steps for the compounds of the invention according to the reactions as described above are shown in the following scheme 1: The compounds of formula (II) are prepared by reacting a nitrophenylacetic acid derivative of formula (IX) wherein R 1 and R 2 are as defined above with a benzaldehyde derivative of formula (VIII) wherein R 5 and R 6 are as defined above while heating at 100 to 200°C in the presence of a catalytic amount of a basic material such as piperidine, to form a compound of formula (X) wherein R 5 and R 6 are as defined above, followed by reduction. The reaction is performed using the compound of formula (VIII) in an amount of 0.1 to 10 moles, preferably. 0.5 to 2 moles per mole of the compound of formula (IX). The reduction process includes e.g. that using zinc, iron, tin, stannous chloride or the like in an acidic solution such as hydrochloric acid, acetic acid or a catalytic hydrogenation using a catalyst such as palladium carbon, platinum oxide or the like. The process steps by the reactions as described above are shown in the following scheme 2: Pharmaceutically acceptable salts of the compounds of formula (I) may be formed in conventional way. The acid addition salts may be formed for example by reaction of the base compound of formula (I) with a pharmaceutically acceptable inorganic acid such as hydrochloric, hydrobromic, hydroiodic, sulfuric and phosphoric acids or a pharmaceutically acceptable organic acid such as oxalic, maleic, fumaric, lactic, malic, citric, tartaric, benzoic and methanesulphonic acids. The compounds of formula (I) according to the present invention possess both an ACAT inhibitor activity and an antioxidative activity, especially a protective ability against an oxidative modification of LDL. By the ACAT inhibitory activity, the present compounds can inhibit an absorption of cholesterol from the intestinal tracts, reduce a plasma cholesterol level and inhibit an accumulation of cholesteryl esters in the wall of blood vessels, atheroma lesion and macrophage. By the antioxidative activity, especially a protective activity against the oxidative modification of LDL, the present compounds can inhibit the formation and progression of atherosclerosis lesion and inducing its regression. Thus, the compounds of the present invention are useful in the prophylaxis or treatment of hypercholesterolemia and atherosclerosis. According to another aspect of the present invention, there is provided an ACAT inhibitor comprising the compound of formula (I) or a pharmaceutically acceptable salt thereof. In further aspects, the present invention provides a pharmaceutical composition for the prophylaxis or treatment of hypercholesterolemia or atherosclerosis, which comprises as an active ingredient the compound of formula (I) or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier and/or excipient. The compounds of the invention can usually be administered orally or parenterally in the form of a pharmaceutical preparation. The pharmaceutical preparations include tablets, capsules, troches, syrups, granules, powders, injections, suspensions and the like. It may be in bilayered or multilayered tablet with other drugs. The tablets may also be coated with a conventional coating to form, e.g., sugar-coated, enteric-coated or film-coated tablets. In preparing solid preparations, additives such as lactose, refined sugar, crystalline cellulose, corn starch, calcium phosphate, sorbitol, glycin, carboxymethylcellulose, gum arabic, polyvinylpyrrolidone, hydroxypropylcellulose, polyethylene glycol, stearic acid, magnesium stearate and talc are employed. A vegetable or synthetic wax or fat or a similar base is used in preparing the semi-solid preparations. As additives in preparing the liquid preparations are used, for example, sodium chloride, sorbitol, glycerin, olive oil, almond oil, propylene glycol and ethyl alcohol. The active ingredient is contained in the formulation in an amount of 0.0001-100% by weight, suitably 0.001-50% by weight in the case of formulations for oral administration and 0.0001-10% by weight in the case of formulations for injection based on the weight of the preparations. Route and dosage of administration for the compounds of the invention are not specifically limited and are appropriately chosen depending upon form of the formulation, age and sex of the patient, severity of the disease and other factors. Daily dosage of the active ingredient is 0.01-1000 mg. No adverse toxicological effects are indicated at any of the above dosage ranges. The invention is further illustrated by the following examples. Example 1 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-hexyloxyphenyl)urea A solution of diphenylphosphorylazide (0.93 g, 3.4 mmol), 4-hexyloxybenzoic acid (0.68 g, 3.1 mmol) and triethylamine (0.34 g, 3.4 mmol) in toluene (10 ml) was stirred at room temperature for 3.5 hrs and heated at about 90°C for 2 hrs with stirring. After allowing the mixture to cool (under 0°C), a solution of 4-(2-aminophenethyl)-2,6-di-tert-butylphenol (1.0 g, 3.1 mmol) in toluene (4 ml) was added dropwise. The solution was warmed up to room temperature and stirred overnight. After distilling off the solvent and purification of the residue by a silica gel column chromatography, recrystallization from ethyl acetate/hexane afforded N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-hexyloxyphenyl)urea (1.2 g, 71% yield). m.p. 174-176°C 1 H-NMR(δ ppm, CDCl 3 ) 7.40-7.42(m, 1H), 7.14-7.26(m, 5H), 6.81(s, 2H), 6.76-6.79(m, 2H), 5.98(s, 1H), 5.39(s, 1H), 5.13(s, 1H), 3.88(t, J=7Hz, 2H), 2.83-2.87(m, 2H), 2.76-2.80(m, 2H), 1.70-1.77(m, 2H), 1.38(s, 18H), 1.30-1.45(m, 6H), 0.87-0.93(m, 3H) IR (cm -1 ) 3640, 3310, 2950, 1630, 1560, 1490, 1440, 1230 Example 2 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(8-heptadecenyl)urea The title compound was prepared in a similar manner to that mentioned in Example 1, using 9-octadecenoic acid instead of 4-hexyloxybenzoic acid. 1 H-NMR (δ ppm, CDCl 3 ) 7.16-7.26(m, 4H), 6.78(s, 2H), 5.29-5.34(m, 2H), 5.12(s, 1H), 5.00(s, 1H), 4.19(t, J=6Hz, 1H), 3.11(dd, J=14, 6Hz, 2H), 2.77-2.87(m, 4H), 1.93-2.02(m, 4H), 1.38(s, 18H), 1.18-1.38(m, 25H) IR (cm -1 ) 3642, 3288, 2926, 1639, 1558, 1435, 1233, 750 Example 3 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(7-methoxycarbonylheptyl)urea The title compound was prepared in a similar manner to that mentioned in Example 1, using 8-methoxycarbonyloctanoic acid instead of 4-hexyloxybenzoic acid 1 H-NMR (δ ppm, CDCl 3 ) 7.16-7.26(m, 4H), 6.78(s, 2H), 5.12(s, 1H), 4.98(s, 1H), 4.17(t, J=6Hz, 1H), 3.66(s, 3H), 3.09-3.14(m, 2H), 2.77-2.87(m, 4H), 2.28(t, J=8Hz 2H), 1.53-1.61(m, 2H), 1.38(s, 18H), 1.18-1.30(m, 6H), 0.88(t, J=7Hz, 2H) IR (cm -1 ) 3640, 2928, 1737, 1639, 1547, 1436, 1234 Example 4 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-cycloheptylurea The title compound was prepared in a similar manner to that mentioned in Example 1, using cycloheptanecarboxylic acid instead of 4-hexyloxybenzoic acid. m.p. 177-178°C 1 H-NMR (δ ppm, CDCl 3 ) 7.17-7.26(m, 4H), 6.79(s, 2H), 5.10(s, 1H), 5.05(bs, 1H), 4.19(d, J=8Hz, 1H), 3.75-3.85(m, 1H), 2.80-2.88(m, 2H), 2.75-2.80(m, 2H), 1.83-1.90(m, 2H), 1.38(s, 18H), 1.21-1.58(m, 10H) IR (cm -1 ) 3650, 3300, 2930, 2860, 1630, 1570, 1440, 1240 Example 5 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-phenethylurea The title compound was prepared in a similar manner to that mentioned in Example 1, using 3-phenylpropionic acid instead of 4-hexyloxybenzoic acid. m.p. 197-198°C 1 H-NMR (δ ppm, CDCl 3 ) 7.08-7.25(m, 9H), 6.76(s, 2H), 5.10(s, 1H), 5.00(s, 1H), 4.24(t, J=6Hz, 1H), 3.36-3.41(m, 2H), 2.72-2.80(m, 6H), 1.36(s, 18H) IR (cm -1 ) 3632, 3284, 2954, 1640, 1559, 1436, 1235, 748 Example 6 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(2,2-diphenylethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 1, using 3,3-diphenylpropionic acid instead of 4-hexyloxybenzoic acid. m.p. 179°C 1 H-NMR (δ ppm, CDCl 3 ) 7.09-7.44(m, 12H), 6.97-7.01(m, 1H), 6.78(d, J=8Hz, 1H), 6.72(s, 2H), 5.07(s, 1H), 4.93(s, 1H), 4.23(t, J=6Hz, 1H), 4.15(t, J=8Hz, 1H), 3.77(dd, J=8, 6Hz, 2H), 2.70(s, 4H), 1.35(s, 18H) IR (cm -1 ) 3644, 2930, 1650, 1553, 1510, 1234 Example 7 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(2,6-diisopropylphenyl)urea The title compound was prepared in a similar manner to that mentioned in Example 1, using 2,6-diisopropylbenzoic acid instead of 4-hexyloxybenzoic acid. m.p. 209-210°C 1 H-NMR (δ ppm, DMSO) 8.01(bs, 1H), 7.85(bs, 1H), 7.65(d, J=8Hz, 1H), 7.20-7.24(m, 1H), 7.10-7.14(m, 4H), 6.93-6.97(m, 3H), 6.62(s, 1H), 3.32-3.53(m, 1H), 3.18-3.25(m, 1H), 2.75-2.85(m, 4H), 1.37(s, 18H), 1.13(d, J=7Hz, 12H) IR (cm -1 ) 3612, 3320, 2958, 1646, 1586, 1534, 1435, 1231, 745 Example 8 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(3-cyclohexylpropyl)urea The title compound was prepared in a similar manner to that mentioned in Example 1, using 4-cyclohexylbutanoic acid instead of 4-hexyloxybenzoic acid. m.p. 166°C 1 H-NMR (δ ppm, CDCl 3 ) 7.18-7.26(m, 4H), 6.78(s, 2H), 5.11(s, 1H), 5.02(s, 1H), 4.20(t, 1H), 3.10 (dt, J=6, 7Hz, 2H), 2.83-2.85(m, 2H), 2.76-2.80(m, 2H), 1.56-1.68(m, 4H), 1.38(s, 18H), 1.33-1.43(m, 2H), 1.04-1.30(m, 6H), 0.75-0.88(m, 3H) IR (cm -1 ) 3640, 3316, 2924, 1640, 1558, 1436, 1233, 749 Example 9 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[3-(2-thienyl)propyl]urea The title compound was prepared in a similar manner to that mentioned in Example 1, using 4-(2-thienyl)butanoic acid instead of 4-hexyloxybenzoic acid. m.p. 150°C 1 H-NMR (δ ppm, CDCl 3 ) 7.19-7.27(m, 4H), 7.07(dd, J=4, 1Hz, 1H), 6.87(dd, J=3, 2Hz, 1H), 6.77(s, 2H), 6.71(t, J=2Hz, 1H), 5.11(s, 1H), 4.96(s, 1H), 4.21(t, 1H), 3.20(s, 2H), 2.77-2.87(m, 6H), 1.81(qui, J=7Hz, 2H), 1.37(s, 18H) IR (cm -1 ) 3638, 3286, 2918, 1630, 1570, 1434, 1233, 696 Example 10 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-phenylurea The title compound was prepared in a similar manner to that mentioned in Example 1, using benzoic acid instead of 4-hexyloxybenzoic acid. m.p. 207°C 1 H-NMR (δ ppm, CDCl 3 ) 7.22-7.36(m, 8H), 7.02(t, J=7Hz, 1H), 6.80(s, 2H), 6.02(s, 1H), 5.18(s, 1H), 5.15(s, 1H), 2.79-2.91(m, 4H), 1.38(s, 18H) IR (cm -1 ) 3630, 3350, 2950, 1650, 1600, 1550, 1500, 1230, 750 Example 11 (1) N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]phenyl carbamate To a solution of 4-(2-aminophenethyl)-2,6-di-tert-butylphenol (7.00 g, 21.5 mmol) and diisopropylamine (3.4 ml, 24 mmol) in dichloromethane (50 ml) was added dropwise a solution of phenyl chloroformate (3.60 g, 23.0 mmol) in dichloromethane (10 ml) so that the internal temperature does not exceed 0°C over a ice-cold water bath. The mixture was stirred at the same temperature for 2 hrs, washed with water, dried over MgSO 4 and concentrated. Purification of the residue by a silica gel column chromatography gave a viscous oil of N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]phenyl carbamate (8.16 g, 85.2% yield). 1 H-NMR (δ ppm, CDCl 3 ) 7.63(bs, 1H), 7.34(t, J=8Hz, 2H), 7.08-7.29(m, 6H), 6.80(s, 2H), 5.74(bs, 1H), 5.13(s, 1H), 2.8-2.9(m, 4H), 1.35(s, 18H) (2) N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-decylurea A solution of N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]phenyl carbamate (1.0 g, 2.2 mmol) and decylamine (0.38 g, 2.4 mmol) in xylene (10 ml) was heated under reflux for 2.5 hrs. After distilling off the solvent, purification of the residue by a silica gel column chromatography afforded waxy N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-decylurea (0.93 g, 85% yield). 1 H-NMR (δ ppm, CDCl 3 ) 7.17-7.26(m, 4H), 6.78(s, 2H), 5.11(s, 1H), 4.98(s, 1H), 4.17(t, J=6Hz, 1H), 3.09-3.16(m, 2H), 2.76-2.87(m, 4H), 1.50-2.50(m, 16H), 1.38(s, 18H), 0.87(t, J=7Hz, 3H) IR (cm -1 ) 3650, 3350, 2960, 2930, 2850, 1640, 1570 Example 12 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-heptylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using heptylamine instead of decylamine. m.p. 100°C 1 H-NMR (δ ppm, CDCl 3 ) 7.18-7.27(m, 4H), 6.78(s, 2H), 5.11(s, 1H), 4.99(s, 1H), 4.18(bt, J=5Hz, 1H), 2.89(q, J=6Hz, 2H), 2.79-2.85(m, 4H), 1.38-1.45(m, 2H), 1.38(s, 18H), 1.15-1.30(m, 8H), 0.86(t, J=7Hz, 3H) IR (cm -1 ) 3650, 3320, 2970, 2940, 2870, 1640, 1570, 1440, 1240, 760 Example 13 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(3,7-dimethyl-2,6-octadienyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3,7-dimethyl-2,6-octadienylamine instead of decylamine. m.p. 87.0-87.5°C 1 H-NMR (δ ppm, CDCl 3 ) 7.16-7.30(m, 4H), 6.78(s, 2H), 5.10(s, 1H), 5.05-5.13(m, 1H), 5.02(bs, 2H), 4.05-4.12(m, 1H), 3.75(t, J=6Hz, 2H), 2.80-2.85(m, 2H), 2.75-2.80(m, 2H), 1.95-2.08(m, 2H), 1.89-1.95(m, 2H), 1.65(s, 3H), 1.60(s, 3H), 1.57(s, 3H), 1.37(s, 18H) IR (cm -1 ) 3628, 3312, 2956, 1638, 1585, 1436, 1233, 752 Example 14 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(2,4,4-trimethyl-2-pentyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 2,2,4-trimethyl-2-pentylamine instead of decylamine. m.p. 168-169°C 1 H-NMR (δ ppm, CDCl 3 ) 7.15-7.26(m, 4H), 6.83(s, 2H), 5.09(s, 2H), 4.18(s, 1H), 2.71-2.87(m, 4H), 1.64(s, 2H), 1.39(s, 18H), 1.34(s, 6H), 0.90(s, 9H) IR (cm -1 ) 3640, 3334, 2956, 1645, 1556, 1437, 1365, 1226 Example 15 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(3-ethoxypropyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-ethoxypropylamine instead of decylamine. m.p. 136-137°C 1 H-NMR (δ ppm, CDCl 3 ) 7.16-7.27(m, 4H), 6.79(s, 2H), 5.10(s, 1H), 5.06(s, 1H), 4.78(t, J=5Hz, 1H), 3.40(t, J=6Hz, 2H), 3.32(dd, J=14, 7Hz, 2H), 3.28(q, J=6Hz, 2H), 2.84-2.88(m, 2H), 2.77-2.80(m, 2H), 1.67-1.73(m, 2H), 1.38(s, 18H), 0.99(t, J=7Hz, 3H) IR (cm -1 ) 3600, 3346, 2952, 1638, 1563, 1436, 1288, 1238, 1108, 753 Example 16 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-cyclopentylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using cyclopentylamine instead of decylamine. m.p. 186-187°C 1 H-NMR (δ ppm, CDCl 3 ) 7.15-7.28(m, 4H), 6.79(s, 2H), 5.11(s, 1H), 5.08(s, 1H), 4.17(d, J=7Hz, 1H), 4.01-4.10(m, 1H), 2.76-2.87(m, 4H), 1.89-1.96(m, 2H), 1.50-1.61(m, 4H), 1.39(s, 18H), 1.22-1.29(m, 2H) IR (cm -1 ) 3650, 3350, 2950, 1640, 1580, 1560, 1440, 1240 Example 17 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-cyclohexylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using cyclohexylamine instead of decylamine. m.p. 198-200°C 1 H-NMR(δ ppm, CDCl 3 ) 7.16-7.25(m, 4H), 6.78(s, 2H), 5.14(s, 1H), 4.99(s, 1H), 4.09(d, J=5Hz, 1H), 3.59-3.62(m, 1H), 2.83(d, J=6Hz, 2H), 2.79(d, J=6Hz, 2H), 1.95-1.99(m, 2H), 1.53-1.64(m, 4H), 1.38(s, 18H), 1.26-1.30(m, 2H), 0.96-0.99(m, 2H) IR (cm -1 ) 3290, 2930, 1630, 1561, 1232 Example 18 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-cyclooctylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using cyclooctylamine instead of decylamine. m.p. 174-176°C 1 H-NMR (δ ppm, CDCl 3 ) 7.17-7.24(m, 4H), 6.79(s, 2H), 5.10(s, 1H), 5.05(s, 1H), 4.19(d, J=5Hz, 1H), 3.68-3.98(m, 1H), 2.83(d, J=6Hz, 2H), 2.79(d, J=6Hz, 2H), 1.74-1.81(m, 2H), 1.42-1.58(m, 12H), 1.38(s, 18H) IR (cm -1 ) 3308, 2922, 1630, 1554, 1435, 1233 Example 19 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-adamantylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-adamantanamine instead of decylamine. m.p. 197-199°C 1 H-NMR (δ ppm, CDCl 3 ) 7.14-7.29(m, 4H), 6.83(s, 2H), 5.11(s, 1H), 5.10(s, 1H), 4.06(s, 1H), 2.79-2.85(m, 4H), 1.91-2.05(m, 9H), 1.60-1.70(m, 6H), 1.39(s, 18H) IR (cm -1 ) 3350, 2900, 2850, 1640, 1550, 1440, 1300, 1240 Example 20 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-benzylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using benzylamine instead of decylamine. m.p. 181-183°C 1 H-NMR (δ ppm, CDCl 3 ) 7.15-7.30(m, 9H), 6.77(s, 2H), 5.13(s, 1H), 5.08(s, 1H), 4.54(t, J=6Hz, 1H), 4.33(d, J=6Hz, 2H), 2.82(d, J=6Hz, 2H), 2.78(d, J=6Hz, 2H), 1.35(s, 18H) IR (cm -1 ) 3294, 2956, 1629, 1579, 1435, 1233, 741 Example 21 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-methylphenethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-methylphenethylamine instead of decylamine. m.p. 170-172°C 1 H-NMR (δ ppm, CDCl 3 ) 7.12-7.23(m, 4H), 7.04(d, J=8Hz, 2H), 6.98(d, J=8Hz, 2H), 6.76(s, 2H), 5.09(s, 1H), 4.96(s, 1H), 4.22(t, J=6Hz, 1H), 3.36(q, J=6Hz, 2H), 2.80(d, J=6Hz, 2H), 2.69(t, J=6Hz, 2H), 2.68(d, J=6Hz, 2H), 2.29(s, 3H), 1.36(s, 18H) IR (cm -1 ) 3342, 2950, 1643, 1563, 1435 Example 22 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-methoxyphenethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-methoxyphenethylamine instead of decylamine. m.p. 148-149°C 1 H-NMR (δ ppm, CDCl 3 ) 7.10-7.24(m, 4H), 7.00(d, J=9Hz, 2H), 6.77(d, J=9Hz, 2H), 6.76(s, 2H), 5.09(s, 1H), 4.95(s, 1H), 4.20(t, J=6Hz, 1H), 3.76(s, 3H), 3.33(q, J=6Hz, 2H), 2.80(d, J=6Hz, 2H), 2.77(d, J=6Hz, 2H), 2.67(t, J=6Hz, 2H), 1.36(s, 18H) IR (cm -1 ) 3420, 2960, 1641, 1561, 1525, 1249 Example 23 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-cyclododecylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using cyclododecylamine instead of decylamine. 1 H-NMR (δ ppm, CDCl 3 ) 7.06-7.29(m, 4H), 6.80(s, 2H), 5.10(s, 2H), 4.05(d, J=9Hz, 1H), 3.89(s, 1H), 2.76-2.87(m, 4H), 1.38(s, 18H), 1.20-1.30(m, 22H) IR (cm -1 ) 3650, 3340, 2950, 2920, 1640, 1560, 1440, 1240 Example 24 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-butylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using butylamine instead of decylamine. m.p. 133-134°C 1 H-NMR (δ ppm, CDCl 3 ) 7.16-7.26(m, 4H), 6.78(s, 2H), 5.12(s, 1H), 4.97(s, 1H), 4.16(t, J=6Hz, 1H), 3.11-3.16(m, 2H), 2.77-2.87(m, 4H), 1.38(s, 18H), 1.21-1.34(m, 4H), 0.87(t, J=7Hz, 3H) IR (cm -1 ) 3450, 3320, 2960, 1640, 1570, 1460, 1440, 1250, 1230 Example 25 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[2-(N,N-dibutylamino)ethyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using N,N-dibutylethylenediamine instead of decylamine. 1 H-NMR (δ ppm, CDCl 3 ) 7.18-7.26(m, 4H), 6.80(s, 2H), 5.18(s, 1H), 5.10(s, 1H), 5.02(bs, 1H), 3.17-3.21(m, 2H), 2.76-2.87(m, 4H), 2.40(t, J=6Hz, 2H), 2.24(t, J=7Hz, 4H), 1.38(s, 18H), 1.04-1.26(m, 8H), 0.82(t, J=7Hz, 6H) IR (cm -1 ) 3650, 3360, 2960, 2880, 1640, 1560, 1440, 1240 Further, the hydrochloride of the title compound was prepared in the following manner. Conc. hydrochloric acid (0.17 ml) was added to a solution of the title compound (0.95 g) in ethanol (12 ml). Distilling off the solvent afforded a waxy hydrochloride of the title compound (1.05 g). Example 26 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(3,4-dimethoxyphenethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3,4-dimethoxyphenethylamine instead of decylamine. m.p. 158-160°C 1 H-NMR (δ ppm, CDCl 3 ) 7.10-7.24(m, 4H), 6.76(s, 2H), 6.70-6.75(m, 1H), 6.60-6.65(m, 2H), 5.10(s, 1H), 5.00(s, 1H), 4.27(t, J=6Hz, 1H), 3.83(s, 3H), 3.81(s, 3H), 3.35-3.40(dt, J=6, 7Hz 2H), 2.72-2.84(m, 4H), 2.68(t, J=7Hz 2H), 1.36(s, 18H) IR (cm -1 ) 3628, 3318, 1632, 1562, 1518, 1264, 1234 Example 27 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(3-phenylpropyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-phenylpropylamine instead of decylamine. m.p. 161-162°C 1 H-NMR (δ ppm, CDCl 3 ) 7.13-7.25(m, 7H), 7.10(d, J=8Hz, 2H), 6.77(s, 2H), 5.10(s, 1H), 4.98(s, 1H), 4.20(t, J=7Hz, 1H), 3.17(q, J=7Hz, 2H), 2.83(d, J=6Hz, 2H), 2.79(d, J=6Hz, 2H), 2.56(t, J=7Hz, 2H), 1.74(qui, J=7Hz, 2H), 1.36(s, 18H) IR (cm -1 ) 3628, 3328, 2952, 1637, 1562, 1435, 1234, 748, 697 Example 28 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-chlorophenethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-chlorophenethylamine instead of decylamine. m.p. 173-174°C 1 H-NMR (δ ppm, CDCl 3 ) 7.09-7.20(m, 6H), 7.02(d, 2H), 6.75(s, 2H), 5.10(s, 1H), 4.91(s, 1H), 4.16(t, J=6Hz, 1H), 3.35(q, J=6Hz, 2H), 2.78(q, J=5Hz, 4H), 2.70(t, J=7Hz, 2H), 1.35(s, 18H) IR (cm -1 ) 3626, 3322, 2950, 1638, 1561, 1493, 1436, 1234 Example 29 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-diphenylmethylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using benzhydrylamine instead of decylamine. m.p. 187.4°C 1 H-NMR (δ ppm, CDCl 3 ) 7.14-7.33(m, 14H), 6.75(s, 2H), 6.10(d, J=8Hz, 1H), 5.17(s, 1H), 5.08(s, 1H), 4.86(d, J=8Hz, 1H), 2.73-2.81(m, 4H), 1.35(s, 18H) IR (cm -1 ) 2960, 1640, 1560, 1500, 1460, 1440, 1240, 740, 700 Example 30 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[(2-furyl)methyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 2-aminomethylfuran instead of decylamine. m.p. 169.7°C 1 H-NMR (δ ppm, CDCl 3 ) 7.15-7.28(m, 5H), 6.76(s, 2H), 6.26-6.27(m, 1H), 6.14-6.15(m, 1H), 5.10(s, 1H), 4.99(s, 1H), 4.45(t, J=6Hz, 1H), 4.32(d, J=6Hz, 2H), 2.76-2.86(m, 4H), 1.36(s, 18H) IR (cm -1 ) 3320, 2950, 1640, 1590, 1570, 1460, 1440, 1240, 730 Example 31 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-phenylbutyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-phenylbutylamine instead of decylamine. m.p. 157.0°C 1 H-NMR (δ ppm, CDCl 3 ) 7.11-7.27(m, 9H), 6.77(s, 2H), 5.10(s, 1H), 4.95(s, 1H), 4.15(t, 1H), 3.12-3.17(m, 2H), 2.74-2.86(m, 4H), 2.58(t, J=8Hz, 2H), 1.39-1.61(m, 4H), 1.37(s, 18H) IR (cm -1 ) 3300, 2950, 2860, 1620, 1600, 1580, 1440, 1250, 1240 Example 32 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[3-(1-imidazolyl)propyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using N-(3-aminopropyl)imidazole instead of decylamine. m.p. 163.5°C 1 H-NMR (δ ppm, CDCl 3 ) 7.39(s, 1H), 7.20-7.29(m, 4H), 7.01(s, 1H), 6.85-6.86(m, 1H), 6.77(s, 2H), 5.15(s, 1H), 4.97(s, 1H), 4.25(t, J=6Hz, 1H), 3.92(t, J=7Hz, 2H), 3.13(dt, J=8, 7Hz, 2H), 2.77-2.86(m, 4H), 1.88-1.95(m, 2H), 1.37(s, 18H) IR (cm -1 ) 3360, 3320, 2960, 1640, 1570, 1520, 1440, 1240 Example 33 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[2-(2-pyridyl)ethyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 2-(2-aminoethyl)pyridine instead of decylamine. m.p. 179.7°C 1 H-NMR (δ ppm, CDCl 3 ) 8.32(d, J=4Hz, 1H), 7.52-7.56(m, 1H), 7.06-7.27(m, 6H), 6.77(s, 2H), 5.21(t, J=6Hz, 1H), 5.11(s, 1H), 5.10(s, 1H), 3.56(q, J=6Hz, 2H), 2.93(t, J=6Hz, 2H), 2.67-2.83(m, 4H), 1.37(s, 18H) IR (cm -1 ) 3350, 2960, 1650, 1590, 1570, 1440, 760 Example 34 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(4-fluorophenyl)-2-methyl-2-propyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-fluoro-α,α dimethylphenethylamine instead of decylamine. m.p. 150.6°C 1 H-NMR (δ ppm, CDCl 3 ) 6.84-7.26(m, 8H), 6.80(s, 2H), 5.10(s, 1H), 5.09(s, 1H), 3.95(s, 1H), 2.95(s, 2H), 2.72-2.82(m, 4H), 1.37(s, 18H), 1.25(s, 6H) IR (cm -1 ) 3350, 2960, 1640, 1560, 1510, 1440, 1240 Example 35 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-benzyl-4-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-benzylpiperidine instead of decylamine. m.p. 79-81°C 1 H-NMR (δ ppm, CDCl 3 ) 7.20-7.34(m, 9H), 6.77(s, 2H), 5.10(s, 1H), 4.99(s, 1H), 4.07-4.15(m, 1H), 3.58-3.72(m, 1H), 3.44(s, 2H), 2.68-2.86(m, 6H), 2.00-2.10(m, 2H), 1.80-1.90(m, 2H), 1.37(s, 18H), 1.24-1.35(m, 2H) IR (cm -1 ) 3632, 3350, 1640, 1552 Example 36 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[2-(3-indolyl)ethyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-(2-aminoethyl)indole instead of decylamine. m.p. 193-194°C 1 H-NMR (δ ppm, CDCl 3 ) 7.92(s, 1H), 7.54(d, J=8Hz, 1H), 7.33(d, J=8Hz, 1H), 7.05-7.26(m, 6H), 6.90(d, J=2Hz, 1H), 6.77(s, 2H), 5.10(s, 1H), 5.00(s, 1H), 4.32(t, J=6Hz, 1H), 3.47(dt, J=6, 7Hz, 2H), 2.90(t, J=7Hz, 2H), 2.73-2.81(m, 4H), 1.35(s, 18H) IR (cm -1 ) 3430, 3340, 2880, 1640, 1560, 1440, 1240, 750 Example 37 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1,2,3,4-tetrahydro-1-naphthyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 1,2,3,4-tetrahydro-1-naphthylamine instead of decylamine. m.p. 168-169°C 1 H-NMR (δ ppm, CDCl 3 ) 7.01-7.27(m, 8H), 6.77(s, 2H), 5.08(s, 1H), 5.01-5.06(m, 2H), 4.42(d, J=8Hz, 1H), 2.65-2.90(m, 6H), 1.50-2.10(m, 4H), 1.35(s, 18H) IR (cm -1 ) 3650, 3350, 2960, 1640, 1560, 1440, 1240 Example 38 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(2-ethylthioethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 2-ethylthioethylamine instead of decylamine. m.p. 131-132°C 1 H-NMR (δ ppm, CDCl 3 ) 7.19-7.28(m, 4H), 6.78(s, 2H), 5.12(s, 1H), 5.03(s, 1H), 4.63(t, J=6Hz, 1H), 3.33(dt, J=6, 7Hz, 2H), 2.80-2.85(m, 4H), 2.60(t, J=7Hz, 2H), 2.48(q, J=7Hz, 2H), 1.38(s, 18H), 1.20(t, J=7Hz, 3H) IR (cm -1 ) 3570, 3320, 2950, 2920, 1640, 1570, 1440, 1250, 1240 Example 39 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(3,9-dimethyl-3,9-diazabicyclo[3.3.1]-7-nonyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 7-amino-3,9-dimethyl-3,9-diazabicyclo[3.3.1]nonane instead of decylamine. 1 H-NMR (δ ppm, CDCl 3 ) 8.55(d, J=10Hz, 1H), 7.14-7.27(m, 4H), 6.85(s, 2H), 5.14(s, 1H), 5.09(s, 1H), 4.10-4.26(m, 1H), 2.87-2.90(m, 2H), 2.77-2.80(m, 2H), 2.70(bs, 2H), 2.41(s, 3H), 2.19-2.38(m, 7H), 1.39(s, 18H), 1.23-1.37(m, 4H) IR(cm -1 ) 3638, 2926, 1651, 1509, 1435, 1377, 733 Example 40 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-benzyl-N'-heptylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using N-heptylbenzylamine instead of decylamine. 1 H-NMR (δ ppm, CDCl 3 ) 7.7-7.75(m, 1H), 6.9-7.3(m, 8H), 6.78(s, 2H), 5.96(s, 1H), 5.06(s, 1H), 4.49(s, 2H), 3.30(t, J=8Hz, 2H), 2.65-2.69(m, 2H), 2.51-2.54(m, 2H), 1.59-1.63(m, 2H), 1.38(s, 18H), 1.22-1.28(m, 8H), 0.86(t, J=7Hz, 3H) IR (cm -1 ) 3640, 2960, 2940, 2870, 1660, 1530, 1460, 1440, 1240, 760 Example 41 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-heptyl-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using N-methylheptylamine instead of decylamine. 1 H-NMR (δ ppm, CDCl 3 ) 7.36(d, J=8Hz, 1H), 7.18-7.22(m, 2H), 7.07-2.10(m, 1H), 6.81(s, 2H), 5.66(s, 1H), 5.08(s, 1H), 3.23(t, J=8Hz, 2H), 2.82(s, 4H), 2.71(s, 3H), 1.45-1.55(s, 2H), 1.36(s, 18H), 1.20-1.30(m, 8H), 0.86(t, J=7Hz, 3H) IR (cm -1 ) 2880, 2870, 2820, 1660, 1520, 1490, 1450, 1440, 1250, 760 Example 42 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N',N'-dibenzylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using N,N-dibenzylamine instead of decylamine. 1 H-NMR (δ ppm, CDCl 3 ) 7.69(d, J=8Hz, 1H), 7.15-7.29(m, 10H), 7.00(m, 1H), 6.90(t, J=8Hz, 1H), 6.80(d, J=8Hz, 1H), 6.74(s, 2H), 6.01(bs, 1H), 5.05(s, 1H), 4.54(s, 4H), 2.59(t, J=8Hz, 2H), 2.38(t, J=8Hz, 2H), 1.37(s, 18H) IR (cm -1 ) 3628, 3280, 2958, 1710, 1645, 1594, 1498, 1475, 1362, 1231, 754, 696 Example 43 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-cyclohexyl-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using N-methylcyclohexylamine instead of decylamine. Amorphous powders. 1 H-NMR (δ ppm, CDCl 3 ) 7.65(d, J=7Hz, 1H), 7.15-7.21(m, 2H), 7.06(t, J=7Hz, 1H), 6.81(s, 2H), 5.68(bs, 1H), 5.08(s, 1H), 4.13(m, 1H), 2.82(s, 4H), 2.54(s, 3H), 1.75-1.81(m, 2H), 1.60-1.75(m, 3H), 1.25-1.40(m, 23H) IR (cm -1 ) 3638, 3426, 2930, 1639, 1520, 1484, 1450, 1314, 1249, 1166, 1121, 751 Example 44 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(9-anthryl)methyl-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using 9-(methylaminomethyl)anthracene instead of decylamine. m.p. 205-206°C 1 H-NMR (δ ppm, CDCl 3 ) 8.47(s, 1H), 8.37(d, J=9Hz, 2H), 8.02-8.04(m, 2H), 7.70(d, J=8Hz, 1H), 7.43-7.57(m, 4H), 7.15-7.31(m, 3H), 6.67(s, 2H), 5.67(s, 1H), 5.59(s, 2H), 4.94(s, 1H), 2.76-2.86(m, 4H), 2.34(s, 3H), 1.19(s, 18H) IR (cm -1 ) 3420, 2950, 1640, 1520, 1490, 1450, 1440, 1250, 740 Example 45 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N',N'-dioctylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using N,N-dioctylamine instead of decylamine. m.p. 55-60°C 1 H-NMR (δ ppm, CDCl 3 ) 7.73(dd, J=8, 1Hz, 1H), 7.13-7.25(m, 2H), 7.00-7.05(m, 1H), 6.85(s, 2H), 5.94(s, 1H), 5.07(s, 1H), 3.18(t, J=8Hz, 4H), 2.81(s, 4H), 1.51-1.61(m, 4H), 1.39(s, 18H), 1.20-1.34(m, 20H), 0.87(t, J=7Hz, 6H) IR (cm -1 ) 3646, 3420, 3322, 1626, 1511 Example 46 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N',N'-dicyclohexylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using N,N-dicyclohexylamine instead of decylamine. m.p. 149-152°C 1 H-NMR (δ ppm, CDCl 3 ) 7.73(dd, J=8, 1Hz, 1H), 7.15-7.20(m, 1H), 7.13(dd, J=7, 2Hz, 1H), 7.00-7.05(m, 1H), 6.94(s, 2H), 6.15(s, 1H), 5.06(s, 1H), 3.42-3.52(m, 2H), 2.84(s, 4H), 1.55-1.83(m, 14H), 1.41(s, 18H), 1.22-1.34(m, 4H), 0.98-1.13(m, 2H) IR (cm -1 ) 3474, 3400, 1644, 1588, 1517 Example 47 N-[2-(3,5-diisopropyl-4-hydroxyphenethyl)phenyl]-N'-heptylurea A solution of diphenylphosphoryl azide (0.88 g, 3.2 mmol), octanoic acid (0.42 g, 2.9 mmol) and triethylamine (0.32 g, 3.2 mmol) in toluene (10 ml) was stirred at room temperature for 1.5 hrs and further stirred at about 90°C for 2 hrs. After allowing the mixture to cool, a solution of 4-(2-aminophenethyl)-2,6-diisopropylphenol (0.85 g, 2.9 mmol) in toluene (2 ml) was added dropwise under ice-cooling while stirring. The reaction solution was returned slowly to room temperature and stirred overnight. The solvent was distilled off, the residue was purified by a silica gel column chromatography and recrystallized from ethyl acetate/hexane to give crystals of the title compound (0.99 g, 76%). m.p. 150-151°C 1 H-NMR (δ ppm, CDCl 3 ) 7.16-7.26(m, 4H), 6.69(s, 2H), 5.14(s, 1H), 4.73(s, 1H), 4.18(t, J=6Hz, 1H), 3.01-3.15(m, 4H), 2.71-2.89(m, 4H), 1.34-1.44(m, 2H), 1.2-1.3(m, 8H), 1.20,(s, 6H), 1.19(s, 6H), 0.86(t, J=7Hz, 3H) IR (cm -1 ) 3330, 2960, 2930, 1640, 1580, 1470, 1450, 1260, 750 Example 48 N-[2-(3,5-di-tert-butyl-4-hydroxystyryl)phenyl]-N'-heptylurea A solution of diphenylphosphoryl azide (0.36 g, 1.3 mmol), octanoic acid (0.17 g, 1.2 mmol) and triethylamine (0.13 g, 1.3 mmol) in toluene (5 ml) was stirred at room temperature for 1.5 hrs and further stirred at about 90°C for 2 hrs. After allowing the mixture to cool, a solution of 4-(2-aminostyryl)-2,6-di-tert-butylphenol (0.89 g, 1.2 mmol) in toluene (2 ml) was added dropwise under ice-cooling while stirring. The reaction solution was returned slowly to room temperature and stirred overnight. The solvent was distilled off, the residue was purified by a silica gel column chromatography and recrystallized from ethyl acetate/hexane to give crystals of the title compound (0.39 g, 70%). m.p. 162-164°C 1 H-NMR(δ ppm, CDCl 3 ) 7.63(dd, J=7, 2Hz, 1H), 7.33-7.37(m, 3H), 7.21-7.28(m, 2H), 7.08(d, J=16Hz, 1H), 7.01(d, J=16Hz, 1H), 6.01(bs, 1H), 5.33(s, 1H), 4.54(t, J=6Hz, 1H), 3.20(dt, J=6, 7Hz, 2H), 1.42-1.47(m, 20H), 1.20-1.36(m, 8H), 0.83(t, J=7Hz, 3H) IR (cm -1 ) 3626, 3334, 2954, 2926, 1642, 1568, 1454, 1439, 1235, 1152, 960, 751 Example 49 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[2-(4-phenyl-1-piperadinyl)-5-pyridyl]urea The title compound was prepared in a similar manner to that mentioned in Example 1, using 6-(4-phenyl-1-piperadinyl)nicotinic acid instead of 4-hexyloxybenzoic acid. m.p. 197-199°C 1 H-NMR(δ ppm, CDCl 3 ) 7.95(d, J=2Hz, 1H), 7.67(dd, J=9, 2Hz, 1H), 7.39(d, J=9Hz, 1H), 7.17-7.33(m, 5H), 6.94-7.00(m, 2H), 6.89(dd, J=7, 7Hz, 1H), 6.81(s, 2H), 6.65(d, J=9Hz, 1H), 5.85(bs, 1H), 5.22(bs, 1H), 5.16(s, 1H), 3.62(t, J=5Hz, 4H), 3.28(t, J=5Hz, 4H), 2.76-2.92(m, 4H), 1.38(s, 18H) IR(cm -1 ) 3620, 3330, 3290, 2954, 1646, 1600, 1547, 1492, 1233, 951, 760 Example 50 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(dicyclohexylmethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 1, using dicyclohexylacetic acid instead of 4-hexyloxybenzoic acid. m.p. 194-195°C 1 H-NMR(δ ppm, CDCl 3 ) 7.29-7.18(m, 4H), 6.81(s, 2H), 5.19(bs, 1H), 5.09(s, 1H), 4.00(d, J=10Hz, 1H), 3.47(bs, 1H), 2.88(t, J=7Hz, 2H), 2.80(t, J=7Hz, 2H), 1.54-1.70(m, 10H), 1.38(s, 18H), 1.38-1.42(m, 2H), 1.01-1.19(m, 8H), 0.73-0.80(m, 2H) IR(cm -1 ) 3642, 3362, 2924, 2852, 1641, 1553, 1436, 1235, 744 Example 51 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(6-oxoheptyl)urea The title compound was prepared in a similar manner to that mentioned in Example 1, using 7-oxooctanoic acid instead of 4-hexyloxybenzoic acid. m.p. 73-76°C 1 H-NMR(δ ppm, CDCl 3 ) 7.16-7.25(m, 4H), 6.77(s, 2H), 5.12(s, 1H), 4.97(s, 1H), 4.17-4.24(m, 1H), 3.12(td, J=7, 6Hz, 2H), 2.76-2.86(m, 4H), 2.38(t, J=7Hz, 2H), 2.10(s, 3H), 1.49-1.57(m, 2H), 1.33-1.45(m, 4H), 1.37(s, 18H) IR(cm -1 ) 3368, 2950, 1712, 1632, 1574 Example 52 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-tert-butylcyclohexyl)urea The title compound was prepared in a similar manner to that mentioned in Example 1, using 4-tert-butylcyclohexanecarboxylic acid instead of 4-hexyloxybenzoic acid. m.p. 206-208°C 1 H-NMR(δ ppm, CDCl 3 ) 7.15-7.25(m, 4H), 6.78(s, 2H), 5.10(s, 1H), 5.00(s, 1H), 4.02(d, J=8Hz, 1H), 3.47-3.57(m, 1H), 2.76-2.86(m, 4H), 1.96-1.98(m, 2H), 1.70-1.73(m, 2H), 1.38(s, 18H), 0.84-1.13(m, 5H), 0.81(s, 9H) IR(cm -1 ) 3642, 3356, 2948, 1640, 1585, 1436, 1234 Example 53 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-cycloheptyl-N'-heptylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using N-heptylcycloheptylamine instead of decylamine. m.p. 70-72°C 1 H-NMR(δ ppm, CDCl 3 ) 7.77(dd, J=8, 1Hz, 1H), 7.20(ddd, J=8, 8, 2Hz, 1H), 7.13(dd, J=8, 1Hz, 1H), 7.02(ddd, J=8, 8, 1Hz, 1H), 6.89(s, 2H), 6.04(s, 1H), 5.06(s, 1H), 4.02(bs, 1H), 3.07-3.11(m, 2H), 2.82(s, 4H), 1.82-1.87(m, 2H), 1.58-1.70(m, 8H), 1.40-1.56(m, 4H), 1.40(s, 18H), 1.25(bs, 8H), 0.84-0.90(m, 3H) IR(cm -1 ) 3642, 3296, 2910, 1631, 1588, 1435, 1235, 751 Example 54 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-benzyl-N'-cycloheptylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using benzylcycloheptylamine instead of decylamine. m.p. 183-184°C 1 H-NMR(δ ppm, CDCl 3 ) 7.74(d, J=8Hz, 1H), 7.25-7.30(m, 2H), 7.07-7.21(m, 4H), 6.90-6.93(m, 2H), 6.76(s, 2H), 5.95(s, 1H), 5.06(s, 1H), 4.42-4.50(m, 1H), 4.43(s, 2H), 2.52(t, J=8Hz, 2H), 2.23(t, J=8Hz, 2H), 1.92-1.99(m, 2H), 1.43-1.72(s, 10H), 1.42(s, 18H) IR(cm -1 ) 3638, 3402, 2926, 1671, 1589, 1527, 1455, 1232, 1213, 752 Example 55 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[[1-(4-dimethylaminophenyl)cyclopentyl]methyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-[1-(aminomethyl)cyclopentyl]-N,N-dimethylaniline instead of decylamine. m.p. 174-175°C 1 H-NMR(δ ppm, CDCl 3 ) 7.08-7.21(m, 3H), 7.03(d, J=7Hz, 1H), 6.92(d, J=9Hz, 2H), 6.77(s, 2H), 6.54(d, J=8Hz, 2H), 5.07(s, 2H), 4.07-4.15(m, 1H), 3.22(d, J=5Hz, 2H), 2.88(s, 6H), 2.69-2.79(m, 4H), 1.63-1.83(m, 8H), 1.36(s, 18H) IR(cm -1 ) 3640, 3360, 1644, 1525, 1435, 1233, 814, 749 Example 56 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(2-ethyl-1,3-dihydroxy-2-propyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 2-amino-2-ethyl-1,3-propanediol instead of decylamine. m.p. 145-146°C 1 H-NMR(δ ppm, CDCl 3 ) 7.16-7.31(m, 4H), 6.78(s, 2H), 5.12(s, 1H), 5.11(s, 1H), 4.61(s, 1H), 3.75-3.89(m, 4H), 3.46-3.55(m, 2H), 2.75-2.88(m, 4H), 1.51(q, J=8Hz, 2H), 1.38(s, 18H), 0.75(t, J=8Hz, 3H) IR(cm -1 ) 3640, 3570, 3400, 3340, 2970, 1660, 1610, 1560, 1440, 1250, 750, 650 Example 57 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-benzyloxycyclopropyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-benzyloxycyclohexylamine instead of decylamine. m.p. 152-153°C 1 H-NMR(δ ppm, CDCl 3 ) 7.16-7.36(m, 9H), 6.77(s, 2H), 5.11(s, 1H), 4.94(s, 1H), 4.51(s, 2H), 4.00(d, J=8Hz, 1H), 3.56-3.68(m, 1H), 3.18-3.28(m, 1H), 2.74-2.86(m, 4H), 1.93-2.15(m, 4H), 1.31-1.47(m, 2H), 1.38(s, 18H), 0.94-1.08(m, 2H) IR(cm -1 ) 3630, 3370, 3330, 2950, 1645, 1565, 1235, 1090, 750 Example 58 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(2-ethoxycarbonylethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using ethyl 3-aminopropionate instead of decylamine. m.p. 158-159°C 1 H-NMR(δ ppm, CDCl 3 ) 7.14-7.28(m, 4H), 6.78(s, 2H), 5.12(s, 1H), 5.08(s, 1H), 4.75(t, J=6Hz, 1H), 4.07(q, J=7Hz, 2H), 3.41(dt, J=6, 6Hz, 1H), 2.74-2.86(m, 4H), 2.49(t, J=6Hz, 2H), 1.38(18H.s, 18H), 1.18(t, J=7Hz, 3H) IR(cm -1 ) 3630, 3320, 3270, 2960, 1730, 1630, 1570, 1440, 1235, 1190, 745 Example 59 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-aminocyclohexyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 1,4-diaminocyclohexane instead of decylamine. m.p. >280°C (dec.) 1 H-NMR(δ ppm, CDCl 3 ) 7.14-7.28(m, 4H), 6.77(s, 2H), 5.12(bs, 1H), 4.97(bs, 1H), 3.98-4.05(m, 1H), 3.53-3.64(m, 1H), 2.74-2.87(m, 4H), 2.52-2.62(m, 1H), 1.89-1.97(m, 2H), 1.77-1.86(m, 2H), 1.38(s, 18H), 0.97-1.24(m, 4H) IR(cm -1 ) 3630, 3420, 3340, 2940, 1635, 1590, 1570, 1240, 935 Example 60 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-acetamidocyclohexyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using N-(4-aminocyclohexyl)acetamide instead of decylamine. m.p. 250°C (dec.) 1 H-NMR(δ ppm, CDCl 3 ) 7.16-7.30(m, 4H), 6.77(s, 2H), 5.26(bd, J=8Hz, 1H), 5.11(s, 1H), 4.93(s, 1H), 4.05(d, J=8Hz, 1H), 3.54-3.73(m, 2H), 2.74-2.87(m, 4H), 1.92-2.00(m, 4H), 1.93(s, 3H), 1.37(s, 18H), 1.03-1.27(m, 4H) IR(cm -1 ) 3640, 3290, 2950, 1635, 1550, 1440, 1235, 760 Example 61 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-hydroxycyclohexyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-aminocyclohexanol instead of decylamine. m.p. 202-203°C 1 H-NMR(δ ppm, CDCl 3 ) 7.17-7.29(m, 4H), 6.77(s, 2H), 5.12(s, 1H), 4.94(s, 1H), 3.99(d, J=8Hz, 1H), 3.43-3.69(m, 2H), 2.75-2.87(m, 4H), 1.87-2.01(m, 4H), 1.28-1.43(m, 2H), 1.38(s, 18H), 0.97-1.12(m, 2H) IR(cm -1 ) 3645, 3320, 2950, 1640, 1570, 1440, 1235, 1070, 880, 745 Example 62 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-acetoxycyclohexyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-aminocyclohexyl acetate instead of decylamine. m.p. 92-94°C 1 H-NMR(δ ppm, CDCl 3 ) 7.17-7.28(m, 4H), 6.77(s, 2H), 5.12(s, 1H), 4.93(s, 1H), 4.53-4.64(m, 1H), 4.02(d, J=8Hz, 1H), 3.57-3.71(m, 1H), 2.78-2.87(m, 4H), 2.01(s, 3H), 1.87-2.02(m, 4H), 1.32-1.52(m, 2H), 1.38(s, 18H), 1.02-1.16(m, 2H) IR(cm -1 ) 3640, 3380, 2960, 1740, 1645, 1560, 1440, 1245, 1050, 765 Example 63 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(3-pyridylmethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-(aminomethyl)pyridine instead of decylamine. m.p. 163-164°C 1 H-NMR(δ ppm, CDCl 3 ) 8.48(dd, J=5, 1Hz, 1H), 8.45(d, J=2Hz, 1H), 7.58(d, J=8Hz, 1H), 7.18-7.27(m, 5H), 6.75(s, 2H), 5.12(s, 1H), 4.95(s, 1H), 4.45-4.50(m, 1H), 4.34(d, J=6Hz, 2H), 2.75-2.86(m, 4H), 1.35(s, 18H) IR(cm -1 ) 3294, 1634, 1574, 1430, 1239, 1119, 760, 712 Example 64 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-pyridylmethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-(aminomethyl)pyridine instead of decylamine. m.p. 214-215°C 1 H-NMR(δ ppm, CDCl 3 ) 8.50(dd, J=4, 1Hz, 2H), 7.30-7.25(m, 2H), 7.20-7.24(m, 2H), 7.12(d, J=6Hz, 2H), 6.77(s, 2H), 5.13(s, 1H), 5.00(s, 1H), 4.54(t, J=6Hz, 1H), 4.34(d, J=6Hz, 2H), 2.86-2.90(m, 2H), 2.79-2.82(m, 2H), 1.35(s, 18H) IR(cm -1 ) 3292, 1632, 1573, 1436, 1237, 761 Example 65 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(2-pyridylmethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 2-(aminomethyl)pyridine instead of decylamine. m.p. 189-190°C 1 H-NMR(δ ppm, CDCl 3 ) 8.42(dd, J=4, 1Hz, 1H), 7.61(ddd, J=8, 8, 2Hz, 1H), 7.38(dd, J=8, 1Hz, 1H), 7.12-7.24(m, 5H), 6.80(s, 2H), 5.48(bs, 1H), 5.36(t, J=5Hz, 1H), 5.29(s, 1H), 4.47(d, J=6Hz, 2H), 2.78-2.89(m, 4H), 1.36(s, 18H) IR(cm -1 ) 3632, 3612, 3296, 1627, 1576, 1437, 1234, 755 Example 66 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-ethyl-N'-(4-pyridylmethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-(ethylaminomethyl)pyridine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 8.51(dd, J=4, 1Hz, 2H), 7.66(dd, J=8, 1Hz, 1H), 7.09-7.25(m, 5H), 6.79(s, 2H), 5.85(s, 1H), 5.09(s, 1H), 4.50(s, 2H), 3.09(q, J=7Hz, 2H), 2.74-2.82(m, 4H), 1.36(s, 18H), 1.14(t, J=7Hz, 3H) IR(cm -1 ) 3266, 3060, 1630, 1606, 1516, 1492, 1451, 1431, 1269, 755, 746 Example 67 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(8-methyl-8-azabicyclo[3.2.1]-3-octyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-amino-8-methyl-8-azabicyclo[3.2.1]octane instead of decylamine. m.p. 229-230°C 1 H-NMR(δ ppm, CDCl 3 ) 7.27(d, J=4Hz, 1H), 7.13-7.21(m, 3H), 6.79(s, 2H), 5.51(bs, 1H), 5.14(s, 1H), 4.77(bs, 1H), 4.07-4.13(m, 1H), 3.51(bs, 2H), 2.76-2.87(m, 4H), 2.51(s, 3H), 2.13-2.15(m, 2H), 1.89-1.96(m, 6H), 1.38(m, 18H) IR(cm -1 ) 3360, 1645, 1565, 1435, 1240, 745 Example 68 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(2-pyridylmethyl)-N'-(3-pyridylmethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using N-(3-pyridylmethyl)-2-pyridylmethylamine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 9.47(s, 2H), 8.52(d, J=4Hz, 1H), 8.48(dd, J=5, 1Hz, 1H), 7.89(d, J=6Hz, 1H), 7.76(dd, J=8, 1Hz, 1H), 7.67(ddd, J=8, 8, 2Hz, 1H), 7.54(dd, J=8, 2Hz, 1H), 7.23(t, J=7Hz, 2H), 7.14-7.18(m, 1H), 7.02-7.06(m, 2H), 6.97(d, J=8Hz, 1H), 6.93(s, 2H), 5.19(s, 1H), 4.60(s, 2H), 4.37(s, 2H), 2.96-3.05(m, 2H), 2.90-2.94(m, 2H), 1.35(s, 18H) IR(cm -1 ) 3632, 3250, 1661, 1591, 1533, 1480, 1436, 1393, 1362, 1295, 1214, 755 Example 69 (S)-N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(α-ethoxycarbonyl)benzylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using (S)-α-phenylglycine ethyl ester instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.44(d, J=8Hz, 1H), 7.19-7.33(m, 8H), 6.78(s, 2H), 5.90(s, 1H), 5.74(d, J=7Hz, 1H), 5.59(d, J=8Hz, 1H), 5.16(s, 1H), 4.10-4.24(m, 2H), 2.89-2.92(m, 2H), 2.82-2.85(m, 2H), 1.43(s, 18H), 1.21(t, J=7Hz, 3H) IR(cm -1 ) 3636, 3294, 1737, 1643, 1542, 1435, 1233, 1181, 754 Example 70 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-methyl-3-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-amino-1-methylpiperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.45(d, J=8Hz, 1H), 7.16-7.26(m, 3H), 6.92(s, 2H), 6.35(bs, 1H), 5.40(bs, 1H), 5.17(s, 1H), 3.45(bs, 1H), 3.18-3.23(m, 1H), 2.93-3.01(m, 1H), 2.83-2.92(m, 4H), 2.45-2.51(m, 1H), 2.34(s, 3H), 2.18-2.27(m, 1H), 1.82-1.95(m, 1H), 1.60-1.73(m, 3H), 1.46(s, 18H) IR(cm -1 ) 3638, 3250, 1643, 1548, 1436, 1235, 910, 733 Example 71 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-benzyl-N'-(2-pyridylmethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using N-benzyl-2-pyridylmethylamine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 9.20(bs, 1H), 7.92(d, J=4Hz, 1H), 7.78(d, J=7Hz, 1H), 7.52(ddd, J=8, 8, 2Hz, 1H), 7.19-7.30(m, 7H), 7.01-7.05(m, 2H), 6.93(s, 2H), 6.92-6.94(m, 1H), 5.06(s, 1H), 4.60(s, 2H), 4.41(s, 2H), 2.88-3.00(m, 4H), 1.36(s, 18H) IR(cm -1 ) 3620, 3250, 2244, 1657, 1590, 1532, 1453, 1436, 1213, 752, 732 Example 72 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(α-ethoxycarbonyl)benzylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using (R)-α-phenylglycine ethyl ester instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.18-7.35(m, 9H), 6.77(s, 2H), 5.50(d, J=8Hz, 1H), 5.37(d, J=8Hz, 1H), 5.33(s, 1H), 5.09(s, 1H), 4.07-4.18(m, 2H), 2.78-2.84(m, 4H), 1.35(s, 18H), 1.17(t, J=7Hz, 3H) IR(cm -1 ) 3636, 3330, 1739, 1640, 1542, 1436, 1234, 1180, 935, 751, 698 Example 73 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-azabicyclo[2.2.2]-3-octyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-amino-1-azabicyclo[2.2.2]octane instead of decylamine. m.p. 227-229°C 1 H-NMR(δ ppm, CDCl 3 ) 7.21-7.27(m, 4H), 6.77(s, 2H), 5.11(s, 1H), 5.07(s, 1H), 4.43(d, J=7Hz, 1H), 3.78-3.85(m, 1H), 3.28(ddd, J=14, 10, 2Hz, 1H), 2.65-2.89(m, 8H), 2.29-2.33(m, 1H), 1.85-1.87(m, 1H), 1.55-1.70(m, 4H), 1.38(s, 18H) IR(cm -1 ) 3636, 3368, 3260, 1640, 1587, 1564, 1434, 1237, 1122, 765, 753 Example 74 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[2-(3,4-dichlorophenyl)-2-propyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3,4-dichloro-α,α-dimethylbenzylamine instead of decylamine. m.p. 203-205°C 1 H-NMR(δ ppm, CDCl 3 ) 7.41(d, J=2Hz, 1H), 7.16-7.32(m, 6H), 6.81(s, 2H), 5.17(s, 1H), 5.11(s, 1H), 4.60(s, 1H), 2.79-2.83(m, 4H), 1.56(s, 6H), 1.39(s, 18H) IR(cm -1 ) 3638, 3352, 3282, 1644, 1564, 1558, 1437, 1235, 1171, 1030, 768, 745 Example 75 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-dimethylaminophenethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-dimethylaminophenethylamine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.11-7.24(m, 4H), 6.96(d, J=9Hz, 2H), 6.77(s, 2H), 6.62(s, 2H), 5.09(s, 1H), 5.08(s, 1H), 4.03(t, J=6Hz, 1H), 3.33(td, J=7, 6Hz, 2H), 2.89(s, 6H), 2.72-2.86(m, 4H), 2.64(t, J=7Hz, 2H), 1.37(s, 18H) IR(cm -1 ) 3640, 3342, 2940, 1640, 1562, 1521, 1439, 1232, 660, 643 Example 76 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[[1-(3,4-methylenedioxyphenyl)cyclopentyl]methyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 5-[1-(aminomethyl)cyclopentyl]-1,3-dioxaindane instead of decylamine. m.p. 188-189°C 1 H-NMR(δ ppm, CDCl 3 ) 7.12-7.22(m, 3H), 7.03(d, J=7Hz, 1H), 6.75(s, 2H), 6.59(d, J=2Hz, 1H), 6.57(d, J=8Hz, 1H), 6.47(dd, J=8, 2Hz, 1H), 5.88(s, 2H), 5.08(s, 1H), 5.00(s, 1H), 3.95-4.00(m, 1H), 3.21(d, J=5Hz, 2H), 2.70-2.80(m, 4H), 1.55-1.85(m, 8H), 1.36(s, 18H) IR(cm -1 ) 3640, 3388, 3328, 1645, 1561, 1488, 1435, 1363, 1234, 1042, 940, 760 Example 77 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[2-(3,4-dichlorophenyl)-2-methylpropyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3,4-dichloro-β,β-dimethylphenethylamine instead of decylamine. m.p. 165-167°C 1 H-NMR(δ ppm, CDCl 3 ) 6.95-7.29(m, 7H), 6.73(s, 2H), 5.09(s, 1H), 4.90-5.00(m, 1H), 3.96(bs, 1H), 3.29(d, J=6Hz, 2H), 2.65-2.75(m, 4H), 1.35(s, 18H), 1.23(s, 6H) IR(cm -1 ) 3638, 3364, 1646, 1587, 1563, 1475, 1437, 1235, 762 Example 78 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-methyl-N'-(1-methyl-4-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-methyl-4-(methylamino)piperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.63(d, J=7Hz, 1H), 7.19-7.26(m, 2H), 7.10(ddd, J=7, 7, 1Hz, 1H), 6.79(s, 2H), 5.63(s, 1H), 5.08(s, 1H), 4.20-4.27(m, 1H), 2.85-2.90(m, 2H), 2.82(s, 4H), 2.48(s, 3H), 2.28(s, 3H), 1.98-2.07(m, 2H), 1.55-1.90(m, 4H), 1.35(s, 18H) IR(cm -1 ) 3424, 1638, 1511, 1484, 1450, 1436, 1287, 1042, 754 Example 79 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-fluorophenethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-fluorophenethylamine instead of decylamine. m.p. 177-179°C 1 H-NMR(δ ppm, CDCl 3 ) 7.03-7.26(m, 6H), 6.89-6.93(m, 2H), 6.76(m, 2H), 5.10(s, 1H), 4.94(s, 1H), 4.15-4.20(m, 1H), 3.35(q, J=7Hz, 2H), 2.76-2.82(m, 4H), 2.71(t, J=7Hz, 2H), 1.36(s, 18H) IR(cm -1 ) 3636, 3348, 1643, 1563, 1511, 1438, 1234, 831, 747 Example 80 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(2,4-difluorobenzyl)-4-pyperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(2,4-difluorobenzyl)pyperidine instead of decylamine. m.p. 157-158°C 1 H-NMR(δ ppm, CDCl 3 ) 7.15-7.36(m, 5H), 6.89-6.72(m, 4H), 5.11(s, 1H), 4.97(s, 1H), 4.09(d, J=8Hz, 1H), 3.57-3.72(m, 1H), 3.47(s, 2H), 2.68-2.88(m, 6H), 2.14-2.20(m, 2H), 1.82-1.95(m, 2H), 1.58-1.74(m, 2H), 1.20-1.40(m, 2H), 1.37(s, 18H) IR(cm -1 ) 3640, 3370, 3250, 2960, 1690, 1650, 1590, 1565, 1505, 1235, 850, 760 Example 81 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(4-methoxybenzyl)-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(4-methoxybenzyl)piperidine instead of decylamine. m.p. 152-153°C 1 H-NMR(δ ppm, CDCl 3 ) 7.14-7.30(m, 6H), 6.74-6.88(m, 4H), 5.11(s, 1H), 4.97(s, 1H), 4.09(d, J=8Hz, 1H), 3.79(s, 3H), 3.56-3.72(m, 1H), 3.38(s, 2H), 2.67-2.88(m, 6H), 1.96-2.09(m, 2H), 1.82-1.92(m, 2H), 1.37(s, 18H), 1.18-1.35(m, 2H) IR(cm -1 ) 3640, 3360, 3260, 2950, 1645, 1595, 1565, 1515, 1245, 1045, 760 Example 82 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-phenethyl-4-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-phenethylpiperidine instead of decylamine. m.p. 175-176°C 1 H-NMR(δ ppm, CDCl 3 ) 7.15-7.31(m, 9H), 6.78(s, 2H), 5.12(s, 1H), 5.01(s, 1H), 4.13(d, J=8Hz, 1H), 3.58-3.73(m, 1H), 2.72-2.91(m, 8H), 2.50-2.57(m, 2H), 2.05-2.16(m, 2H), 1.38(s, 18H), 1.24-1.35(m, 2H) IR(cm -1 ) 3640, 3340, 2950, 1640, 1590, 1565, 1435, 1235, 770, 750, 700 Example 83 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(4-fluorobenzyl)-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(4-fluorobenzyl)piperidine instead of decylamine. m.p. 174-175°C 1 H-NMR(δ ppm, CDCl 3 ) 7.16-7.29(m, 6H), 6.93-7.00(m, 2H), 6.77(s, 2H), 5.11(s, 1H), 4.97(s, 1H), 4.09(d, J=8Hz, 1H), 3.57-3.71(m, 1H), 3.39(s, 2H), 2.66-2.87(m, 6H), 1.98-2.08(m, 2H), 1.82-1.90(m, 2H), 1.37(s, 18H), 1.22-1.34(m, 2H) IR(cm -1 ) 3645, 3370, 2950, 1540, 1590, 1560, 1510, 1225, 750 Example 84 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(4-cyanobenzyl)-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(4-cyanobenzyl)piperidine instead of decylamine. m.p. 197-198°C 1 H-NMR(δ ppm, CDCl 3 ) 7.58(d, J=8Hz, 2H), 7.40(d, J=8Hz, 2H), 7.17-7.29(m, 4H), 6.77(s, 2H), 5.12(s, 1H), 4.97(s, 1H), 4.10(d, J=8Hz, 1H), 3.59-3.72(m, 1H), 3.48(s, 2H), 2.75-2.87(m, 4H), 2.64-2.73(m, 2H), 2.03-2.13(m, 2H), 1.83-1.91(m, 2H), 1.37(s, 18H), 1.23-1.35(m, 2H) IR(cm -1 ) 3580, 3355, 3250, 2960, 2240, 1645, 1590, 1560, 1235, 825, 765, 550 Example 85 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-[2,4-bis(trifluoromethyl)benzyl]-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-[2,4-bis(trifluoromethyl)benzyl]piperidine instead of decylamine. m.p. 156-157°C 1 H-NMR(δ ppm, CDCl 3 ) 7.92(d, J=8Hz, 1H), 7.85(s, 1H), 7.73(d, J=8Hz, 1H), 7.17-7.29(m, 4H), 6.78(s, 2H), 5.12(s, 1H), 4.98(s, 1H), 4.11(d, J=8Hz, 1H), 3.61-3.74(m, 1H), 3.64(s, 2H), 2.75-2.88(m, 4H), 2.64-2.73(m, 2H), 2.13-2.23(m, 2H), 1.84-1.92(m, 2H), 1.38(s, 18H), 1.27-1.36(m, 2H) IR(cm -1 ) 3645, 3350, 2955, 1600, 1565, 1440, 1350, 1280, 1175, 1130, 1060, 750, 680 Example 86 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(3-pyridylmethyl)-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(3-pyridylmethyl)piperidine instead of decylamine. m.p. 156-158°C 1 H-NMR(δ ppm, CDCl 3 ) 8.46-8.52(m, 2H), 7.60(d, J=8Hz, 1H), 7.16-7.28(m, 5H), 6.77(s, 2H), 5.12(s, 1H), 5.02(s, 1H), 4.13(d, J=8Hz, 1H), 3.58-3.72(m, 1H), 3.45(s, 2H), 2.67-2.87(m, 6H), 2.03-2.12(m, 2H), 1.82-1.90(m, 2H), 1.37(s, 18H), 1.22-1.37(m, 2H) IR(cm -1 ) 3632, 3362, 2950, 1645, 1561, 1433, 1232, 759, 713 Example 87 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(4-pyridylmethyl)-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(4-pyridylmethyl)piperidine instead of decylamine. m.p. 156-158°C 1 H-NMR(δ ppm, CDCl 3 ) 8.51(dd, J=4, 2Hz, 2H), 7.16-7.28(m, 6H), 6.77(s, 2H), 5.12(s, 1H), 5.00(s, 1H), 4.12(d, J=8Hz, 1H), 3.60-3.72(m, 1H), 3.44(s, 2H), 2.74-2.88(m, 4H), 2.66-2.74(m, 2H), 2.04-2.14(m, 2H), 1.83-1.92(m, 2H), 1.38(s, 18H), 1.25-1.38(m, 2H) IR(cm -1 ) 3630, 3292, 2948, 1620, 1560, 1435, 1237, 1109, 759 Example 88 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(4-diethylaminobenzyl)-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(4-diethylaminobenzyl)piperidine instead of decylamine. m.p. 138-141°C 1 H-NMR(δ ppm, CDCl 3 ) 7.16-7.27(m, 4H), 7.09(d, J=8Hz, 2H), 6.77(s, 2H), 6.60(d, J=8Hz, 2H), 5.11(s, 1H), 4.99(s, 1H), 4.12(bd, J=7Hz, 1H), 3.58-3.70(m, 1H), 3.28-3.40(m, 6H), 2.73-2.86(m, 6H), 1.98-2.08(m, 2H), 1.82-1.89(m, 2H), 1.37(s, 18H), 1.25-1.37(m, 2H), 1.14(t, J=7Hz, 6H) IR(cm -1 ) 3630, 3410, 2950, 1641, 1553, 1520, 1232, 758 Example 89 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(2-pyridylmethyl)-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(2-pyridylmethyl)piperidine instead of decylamine. m.p. 106-109°C 1 H-NMR(δ ppm, CDCl 3 ) 8.54(d, J=4Hz, 1H), 7.58-7.65(m, 1H), 7.33(d, J=8Hz, 1H), 7.12-7.27(m, 6H), 6.77(s, 2H), 5.11(s, 1H), 5.01(s, 1H), 4.14(d, J=7Hz, 1H), 3.61-3.73(m, 1H), 3.59(s, 2H), 2.70-2.86(m, 6H), 2.12-2.21(m, 2H), 1.83-1.91(m, 2H), 1.37(s, 18H), 1.30-1.42(m, 2H) IR(cm -1 ) 3630, 3330, 2948, 1639, 1589, 1543, 1436, 1233, 1121, 756 Example 90 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(cyclohexylmethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using aminomethylcyclohexane instead of decylamine. m.p. 208-210°C 1 H-NMR(δ ppm, CDCl 3 ) 7.18-7.24(m, 4H), 6.78(s, 2H), 5.11(s, 1H), 4.98(bs, 1H), 4.18-4.28(m, 1H), 2.97(t, J=6Hz, 2H), 2.74-2.90(m, 4H), 1.55-1.70(m, 5H), 1.38(s, 18H), 1.08-1.30(m, 4H), 0.78-0.90(m, 2H) IR(cm -1 ) 3616, 3304, 2922, 1627, 1579, 1435, 1233 Example 91 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-benzyl-4-pyperidyl)-N'-(3-pyridylmethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-benzyl-4-(3-pyridylmethylamino)piperidine instead of decylamine. m.p. 127-130°C 1 H-NMR(δ ppm, CDCl 3 ) 8.55(d, J=2Hz, 1H), 8.41(dd, J=5, 2Hz, 1H), 7.65(d, J=8Hz, 1H), 7.59(d, J=8Hz, 1H), 7.13-7.30(m, 6H), 7.18(m, 1H), 7.10(dd, J=8, 5Hz, 1H), 7.01(d, J=4Hz, 2H), 6.75(s, 2H), 5.90(bs, 1H), 5.11(s, 1H), 4.45(s, 2H), 4.22-4.33(m, 1H), 3.47(s, 2H), 2.86-2.97(m, 2H), 2.61(t, J=7Hz, 2H), 2.44(t, J=7Hz, 2H), 2.00-2.14(m, 2H), 1.60-1.86(m, 4H), 1.38(s, 18H) IR(cm -1 ) 3450, 3290, 1628, 1512, 1264, 1121, 1029, 742 Example 92 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-benzyl-4-piperidyl)-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-benzyl-4-(methylamino)piperidine instead of decylamine. m.p. 144-146°C 1 H-NMR(δ ppm, CDCl 3 ) 7.62(d, J=8Hz, 1H), 7.10-7.30(m, 7H), 7.10(d, J=7Hz, 1H), 6.78(s, 2H), 5.62(bs, 1H), 5.08(s, 1H), 4.23(s, 1H), 3.48(s, 2H), 2.86-2.98(m, 2H), 2.81(s, 4H), 2.50(s, 3H), 1.98-2.10(m, 2H), 1.50-1.70(m, 4H), 1.35(s, 18H) IR(cm -1 ) 3328, 2954, 1632, 1512, 1196, 1041, 755, 701 Example 93 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-benzyl-4-piperidyl)-N'-cycloheptylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-benzyl-4-(cycloheptylamino)piperidine instead of decylamine. m.p. 107-109°C 1 H-NMR(δ ppm, CDCl 3 ) 7.72(d, J=8Hz, 1H), 7.23-7.36(m, 5H), 7.19(t, J=7Hz, 1H), 7.13(d, J=6Hz, 1H), 7.02(t, J=7Hz, 1H), 6.93(s, 2H), 6.12(bs, 1H), 5.05(s, 1H), 4.04-4.154(m, 1H), 3.49(s, 2H), 3.37-3.50(m, 1H), 2.90-3.00(m, 2H), 2.84(s, 4H), 1.97-2.10(m, 4H), 1.78-1.89(m, 4H), 1.20-1.65(m, 28H) IR(cm -1 ) 3476, 2922, 1662, 1528, 1454, 1236, 753 Example 94 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-acetyl-4-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-acetyl-4-aminopiperidine instead of decylamine. m.p. 218-221°C 1 H-NMR(δ ppm, CDCl 3 ) 7.15-7.29(m, 4H), 6.76(s, 2H), 5.13(s, 1H), 4.93(bs, 1H), 4.43-4.52(m, 1H), 4.05-4.13(m, 1H), 3.76-3.90(m, 1H), 3.66-3.73(m, 1H), 3.04-3.14(m, 1H), 2.71-2.85(m, 4H), 2.58-2.70(m, 1H), 2.05(s, 3H), 1.95-2.06(m, 1H), 1.82-1.90(m, 1H), 1.37(s, 18H), 1.10-1.20(m, 2H) IR(cm -1 ) 3302, 2952, 1629, 1561, 1434, 1234 Example 95 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-ethyl-4-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-ethylpiperidine instead of decylamine. m.p. 182-184°C 1 H-NMR(δ ppm, CDCl 3 ) 7.10-7.30(m, 4H), 6.77(s, 2H), 5.11(s, 1H), 5.00(bs, 1H), 4.14(bd, J=8Hz, 1H), 3.58-3.72(m, 1H), 2.70-2.90(m, 6H), 2.39(q, J=7Hz), 1.97-2.12(m, 2H), 1.85-1.97(m, 2H), 1.37(s, 18H), 1.30-1.40(m, 2H), 1.07(t, J=7Hz, 3H) IR(cm -1 ) 3362, 2950, 1640, 1563, 1435, 1235 Example 96 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-methyl-4-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-methylpiperidine instead of decylamine. m.p. 193-195°C 1 H-NMR(δ ppm, CDCl 3 ) 7.15-7.25(m, 4H), 6.77(s, 2H), 5.12(s, 1H), 4.97(bs, 1H), 4.10(bd, J=8Hz, 1H), 3.58-3.70(m, 1H), 2.70-2.85(m, 6H), 2.25(s, 3H), 2.02-2.12(m, 2H), 1.84-1.93(m, 2H), 1.38(s, 18H), 1.30-1.43(m, 2H) IR(cm -1 ) 3360, 2944, 1639, 1562 Example 97 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(2,2-dimethylpropyl)-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(2,2-dimethylpropyl)piperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.18-7.26(m, 4H), 6.78(s, 2H), 5.11(s, 1H), 5.06(bs, 1H), 4.12(bd, J=8Hz, 1H), 3.53-3.65(m, 1H), 2.75-2.90(m, 4H), 2.60-2.68(m, 2H), 2.22-2.32(m, 2H), 1.98(s, 2H), 1.73-1.83(m, 2H), 1.38(s, 18H), 1.20-1.40(m, 2H), 0.81(s, 9H) IR(cm -1 ) 3322, 2952, 1638, 1536, 1435, 1234 Example 98 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-benzyl-3-pyrrolidinyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-amino-1-benzylpyrrolidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.10-7.30(m, 9H), 6.78(s, 2H), 5.37(bs, 1H), 5.10(s, 1H), 4.71(bd, J=8Hz, 1H), 4.23-4.34(m,1H), 3.55(d, J=13Hz, 1H), 3.50(d, J=13Hz, 1H), 2.70-2.81(m, 6H), 2.49(d, J=4Hz, 2H), 2.14-2.36(m, 2H), 1.37(s, 18H) IR(cm -1 ) 3634, 3304, 2954, 1638, 1559, 1436, 1234, 749, 699 Example 99 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-benzyl-3-piperidyl)-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-amino-1-benzylpiperazine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.59(d, J=8Hz, 1H), 7.15-7.40(m, 7H), 7.08(t, J=7Hz, 1H), 6.79(s, 2H), 5.72(bs, 1H), 5.06(s, 1H), 4.22-4.34(m, 1H), 3.48(s, 2H), 2.70-2.80(m, 6H), 2.58(s, 3H), 1.60-1.90(m, 4H), 1.30-1.46(m, 2H), 1.35(s, 18H) IR(cm -1 ) 3630, 3422, 2940, 1639, 1520, 1485, 1452, 1312, 1249, 1122, 752, 699 Example 100 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-[bis(4-fluorophenyl)methyl]-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-[bis(4-fluorophenyl)methyl]piperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.65-7.80(m, 4H), 7.15-7.30(m, 4H), 7.12(t, J=7Hz, 2H), 6.84(d, J=9Hz, 2H), 6.77(s, 2H), 5.11(s, 1H), 5.01(bs, 1H), 4.13(t, J=7Hz, 2H), 3.75-3.95(m, 3H), 2.91-3.03(m, 2H), 2.75-2.90(m, 4H), 1.92-2.03(m, 2H), 1.25-1.40(m, 2H), 1.37(s, 18H) IR(cm -1 ) 3314, 2948, 1638, 1602, 1544, 1303, 1226, 1153, 768 Example 101 N-[2-(3,5-di-tert-butyl-4-hydroxystyryl)phenyl]-N'-(2-pyridylmethyl)urea (1) To a solution of 4-(2-aminostyryl)-2,6-di-tert-butylphenol (4.85 g, 15.0 mmol) and diisopropylamine (1.72 g, 17.0 mmol) in methylene chloride (30 ml) was added dropwise under ice-cooling phenyl chloroformate (2.51 g, 16.0 mmol). The mixture was stirred for 7 hrs, while returning slowly to room temperature. To the mixture was added diisopropylamine (0.51 g, 5.0 mmol) and added dropwise under ice-cooling diisopropylamine (0.51 g, 5.0 mmol). This mixture was stirred for 3 hrs, while returning slowly to room temperature. The reaction solution was washed with water and a saturated NaCl solution, dried over MgSO 4 and concentrated. Purification of the residue by a silica gel column chromatography gave N-[2-(3,5-di-tert-butyl-4-hydroxystyryl)phenyl]phenyl carbamate (6.65 g, 99%) as a viscous oil. 1 H-NMR(δ ppm, CDCl 3 ) 7.91(b, 1H), 6.90-7.53(m, 13H), 5.35(s, 1H), 1.49(s, 18H) (2) A solution of N-[2-(3,5-di-tert-butyl-4-hydroxystyryl)phenyl]phenyl carbamate (1.00 g, 2.25 mmol) and 2-(aminomethyl)pyridine (0.27 g, 2.50 mmol) in xylene (5 ml) was stirred at 80-100°C for 3 hrs. After distilling off the solvent, purification of the residue by a silica gel column chromatography afforded N-[2-(3,5-di-tert-butyl-4-hydroxystyryl)phenyl]-N'-(2-pyridylmethyl)urea (0.54 g, 71%) as crystals. m.p. 207-210°C 1 H-NMR(δ ppm, CDCl 3 ) 8.37(d, J=4Hz, 1H), 7.59(dd, J=8, 2Hz, 1H), 7.51(d, J=7Hz, 1H), 7.43-7.50(m, 1H), 7.31(s, 2H), 7.16-7.28(m, 3H), 7.17(d, J=16Hz, 1H), 7.02-7.07(m, 1H), 6.99(d, J=16Hz, 1H), 6.68-6.91(m, 1H), 5.79-5.87(m, 1H), 5.32(s, 1H), 4.51(d, J=5Hz, 2H), 1.45(s, 18H) IR(cm -1 ) 3350, 3270, 2960, 1640, 1560, 1475, 1440, 1235, 1010, 755, 740 Example 102 N-[2-(3,5-di-tert-butyl-4-hydroxystyryl)phenyl]-N'-cycloheptylurea The title compound was prepared in a similar manner to that mentioned in Example 101, using cycloheptylamine instead of 2-(aminomethyl)pyridine. m.p. 203-206°C 1 H-NMR(δ ppm, CDCl 3 ) 7.61(d, J=8Hz, 1H), 7.38(d, J=8Hz, 1H), 7.33(s, 2H), 7.18-7.28(m, 2H), 7.06(d, J=16Hz, 1H), 7.00(d, J=16Hz, 1H), 6.05(s, 1H), 5.33(s, 1H), 4.48-4.55(m, 1H), 4.04-4.16(m, 1H), 1.88-2.00(m, 2H), 1.48-1.62(m, 4H), 1.47(s, 18H), 1.22-1.37(m, 2H) IR(cm -1 ) 3630, 3310, 2950, 1630, 1560, 1440, 1235, 960, 745 Example 103 N-[2-(3,5-di-tert-butyl-4-hydroxystyryl)phenyl]-N'-adamantylurea The title compound was prepared in a similar manner to that mentioned in Example 101, using 1-adamantanamine instead of 2-(aminomethyl)pyridine. m.p. 205-211°C 1 H-NMR(δ ppm, CDCl 3 ) 7.66(dd, J=7, 2Hz, 1H), 7.34(s, 2H), 7.29-7.36(m, 1H), 7.15-7.29(m, 2H), 7.06(d, J=16Hz, 1H), 7.00(d, J=16Hz, 1H), 5.90(s, 1H), 5.33(s, 1H), 4.34(s, 1H), 1.82-2.06(m, 9H), 1.52-1.67(m, 6H), 1.47(s, 18H) IR(cm -1 ) 3630, 3330, 2900, 1640, 1560, 1525, 1235, 740, Example 104 N-[2-(3,5-di-tert-butyl-4-hydroxystyryl)phenyl]-N',N'-dibenzylurea The title compound was prepared in a similar manner to that mentioned in Example 101, using N,N-dibenzylamine instead of 2-(aminomethyl)pyridine. m.p. 175-178°C 1 H-NMR(δ ppm, CDCl 3 ) 7.79(dd, J=8, 1Hz, 1H), 7.36(dd, J=8, 1Hz, 1H), 7.02-7.30(m, 13H), 7.02-7.08(m, 1H), 6.78(d, J=16Hz, 1H), 6.65(d, J=16Hz, 1H), 5.31(s, 1H), 4.60(s, 4H), 1.47(s, 18H) IR(cm -1 ) 3420, 3390, 2940, 1660, 1580, 1520, 1450, 1435, 1230, 960, 755 Example 105 N-[2-(3,5-di-tert-butyl-4-hydroxystyryl)phenyl]-N'-methyl-N'-heptylurea The title compound was prepared in a similar manner to that mentioned in Example 101, using N-methylheptylamine instead of 2-(aminomethyl)pyridine. 1 H-NMR(δ ppm, CDCl 3 ) 7.81(d, J=8Hz, 1H), 7.44(d, J=8Hz, 1H), 7.32(s, 2H), 7.22-7.27(m, 1H), 7.05-7.10(m, 1H), 7.00(d, J=16Hz, 1H), 6.93(d, J=16Hz, 1H), 6.36(s, 1H), 5.32(s, 1H), 3.34(d, J=8Hz, 2H), 3.02(s, 3H), 1.54-1.65(m, 2H), 1.47(s, 18H), 1.16-1.32(m, 8H), 0.84(t, J=7Hz, 3H) IR(cm -1 ) 3640, 3450, 3300, 2960, 2930, 1640, 1580, 1520, 1485, 1440, 1240, 1155, 960, 750 Example 106 N-[2-(3,5-di-tert-butyl-4-hydroxystyryl)phenyl]-N'-benzyl-N'-(2-pyridylmethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 101, using 2-(benzylaminomethyl)pyridine instead of 2-(aminomethyl)pyridine. 1 H-NMR(δ ppm, CDCl 3 ) 9.74(b, 1H), 8.14(d, J=4Hz, 1H), 7.87(d, J=8Hz, 1H), 7.47-7.57(m, 1H), 7.18-7.34(m, 9H), 6.88-7.11(m, 4H), 5.26(s, 1H), 4.65(s, 2H), 4.49(s, 2H), 1.40(s, 18H) IR(cm -1 ) 3390, 2950, 1660, 1580, 1525, 1455, 1230, 960, 755, 735, 700 Example 107 N-[2-(3,5-di-tert-butyl-4-hydroxystyryl)phenyl]-N'-(3,9-dimethyl-3,9-diazabicyclo[3-3.1]-7-nonyl)urea The title compound was prepared in a similar manner to that mentioned in Example 101, using 7-amino-3,9-dimethyl-3,9-diazabicyclo[3.3.1]nonane instead of 2-(aminomethyl)pyridine. m.p. 188-191°C 1 H-NMR(δ ppm, CDCl 3 ) 8.78(d, J=10Hz, 1H), 7.64(dd, J=7, 2Hz, 1H), 7.30-7.35(m, 3H), 7.13-7.27(m, 2H), 7.13(d, J=2Hz, 1H), 7.02(d, J=2Hz, 1H), 5.93(s, 1H), 5.35(s, 1H), 4.22-4.33(m, 1H), 2.66-2.72(m, 2H), 2.41(s, 3H), 2.22-2.40(m, 6H), 1.48(s, 3H), 1.47(s, 18H), 1.28-1.38(m, 2H) IR(cm -1 ) 3410, 2940, 1630, 1600, 1510, 1440, 1390, 1265, 1185, 965, 760 Example 108 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-(1-benzyl-4-piperidyl)urea (1) To a solution of 4-(2-amino-3,5-difluorophenethyl)-2,6-di-tert-butylphenol (1.37 g, 3.8 mmol) and diisopropylamine (0.50 g, 4.9 mmol) in methylene chloride (20 ml) was added dropwise under ice-cooling phenyl chloroformate (0.66 g, 4.2 mmol) and the mixture was stirred for 3 hrs, while returning slowly to room temperature. Diisopropylamine (0.19 g, 1.9 mmol) was further added and phenyl chloroformate (0.30 g, 1.9 mmol) was added dropwise under ice-cooling. The mixture was stirred for 3 hrs while returning slowly to room temperature. The reaction solution was washed with water and a saturated NaCl solution, dried over MgSO 4 and concentrated. Purification of the residue by silica gel column chromatography gave N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]phenyl carbamate (1.82 g, 99%) as oil. 1 H-NMR(δ ppm, CDCl 3 ) 7.04-7.42(m, 5H), 6.67-6.85(m, 4H), 5.16(s, 1H), 4.94(s, 1H), 2.76-3.02(m, 4H), 1.37(s, 18H) (2) A solution of N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]phenyl carbamate (1.82 g, 3.8 mmol) and 4-amino-1-benzylpyridine (0.72 g, 3.8 mmol) in toluene (10 ml) was stirred at 100-120°C for 2 hrs. After distilling off the solvent, purification of the residue by a silica gel column chromatography afforded N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-(1-benzyl-4-piperidyl)urea (1.39 g, 64%) as a noncrystalline solid. 1 H-NMR(δ ppm, CDCl 3 ) 7.20-7.30(m, 5H), 6.65-6.80(m, 4H), 5.12(s, 1H), 4.79(bs, 1H), 4.14(bd, J=8Hz, 1H), 3.54-3.66(m, 1H), 3.44(s, 2H), 2.84(d, J=7Hz, 2H), 2.70-2.79(m, 4H), 1.98-2.10(m, 2H), 1.80-1.92(m, 2H), 1.30-1.40(m, 20H) IR(cm -1 ) 3638, 3316, 2952, 1639, 1562, 1494, 1436, 1235, 1122 Example 109 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4-fluorophenyl]-N'-(1-benzyl-4-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 108, using 4-(2-amino-5-fluorophenethyl)-2,6-di-tert-butylphenol instead of 4-(2-amino-3,5-difluorophenethyl)-2,6-di-tert-butylphenol. m.p. 108-109°C 1 H-NMR(δ ppm, CDCl 3 ) 7.21-7.31(m, 5H), 7.16(dd, J=9, 5Hz, 1H), 6.87-6.96(m, 2H), 6.77(s, 2H), 5.12(s, 1H), 4.86(s, 1H), 3.99(d, J=8Hz, 1H), 3.55-3.70(m, 1H), 3.44(s, 1H), 2.70-2.85(m, 6H), 2.05(t, J=11Hz, 2H), 1.85(d, J=10Hz, 2H), 1.38(s, 18H), 1.25-1.35(m, 2H) IR(cm -1 ) 3636, 3280, 1634, 1561, 1495, 1435, 1234, 1213, 1120, 739, 699 Example 110 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-5-fluorophenyl]-N'-(1-benzyl-4-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 108, using 4-(2-amino-4-fluorophenethyl)-2,6-di-tert-butylphenol instead of 4-(2-amino-3,5-difluorophenethyl)-2,6-di-tert-butylphenol. m.p. 118-119°C 1 H-NMR(δ ppm, CDCl 3 ) 7.20-7.32(m, 5H), 7.13-7.20(m, 2H), 6.84(dt, J=3, 8Hz, 1H), 6.78(s, 2H), 5.13(s, 1H), 5.01(s, 1H), 4.02(d, J=8Hz, 1H), 3.46-3.63(m, 1H), 3.46(s, 2H), 2.77(bs, 6H), 2.06(t, J=11Hz, 2H), 1.86(d, J=11Hz, 2H), 1.38(s, 18H), 1.30-1.40(m, 2H) IR(cm -1 ) 3630, 3350, 1640, 1602, 1563, 1434, 1233, 738, 700 Example 111 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4-methoxyphenyl]-N'-(1-benzyl-4-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 108, using 4-(2-amino-5-methoxyphenethyl)-2,6-di-tert-butylphenol instead of 4-(2-amino-3,5-difluorophenethyl)-2,6-di-tert-butylphenol. m.p. 174-175°C 1 H-NMR(δ ppm, CDCl 3 ) 7.20-7.30(m, 5H), 7.00-7.07(m, 1H), 6.78(s, 2H), 6.70-6.75(m, 2H), 5.09(s, 1H), 4.91(s, 1H), 4.05(d, J=8Hz, 1H), 3.79(s, 3H), 3.60-3.65(m, 1H), 3.43(s, 2H), 2.70-2.80(m, 6H), 2.05(t, J=11Hz, 2H), 1.85(d, J=11Hz, 2H), 1.38(s, 18H), 1.20-1.40(m, 2H) IR(cm -1 ) 3630, 3312, 1634, 1561, 1501, 1436, 1282, 1231, 1055, 880, 750, 710 Example 112 N-[4-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-phenylurea The title compound was prepared in a similar manner to that mentioned in Example 1, using 4-(4-aminophenethyl)-2,6-di-tert-butylphenol instead of 4-(2-aminophenethyl)-2,6-di-tert-butylphenol and using benzoic acid instead of 4-hexyloxybenzoic acid. m.p. 206-207°C 1 H-NMR(δ ppm, CDCl 3 ) 7.22-7.38(m, 6H), 7.18(d, J=9Hz, 2H), 7.08-7.14(m, 1H), 6.55(bs, 1H), 6.47(bs, 1H), 2.77-2.92(m, 4H), 1.43(s, 18H) IR(cm -1 ) 3640, 3330, 2960, 1655, 1605, 1565, 1440, 1320, 1240, 760, 695 Example 113 N-[4-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-heptylurea The title compound was prepared in a similar manner to that mentioned in Example 1, using 4-(4-aminophenethyl)-2,6-di-tert-butylphenol instead of 4-(2-aminophenethyl)-2,6-di-tert-butylphenol and n-octanoic acid instead of 4-hexyloxybenzoic acid. m.p. 151-152°C 1 H-NMR(δ ppm, CDCl 3 ) 7.13-7.21(m, 4H), 6.95(s, 2H), 6.22(bs, 1H), 5.06(s, 1H), 4.73(bt, J=5Hz, 1H), 3.23(dt, J=5, 7Hz, 2H), 2.75-2.90(m, 42H), 1.45-1.54(m, 2H), 1.42(s, 18H), 1.21-1.36(m, 8H), 0.88(t, J=7Hz, 3H) IR(cm -1 ) 3630, 3120, 2960, 2930, 2860, 1645, 1605, 1575, 1520, 1440, 1235 Example 114 1-Benzyl-4-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]piperazine The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-benzylpiperazine instead of decylamine. m.p. 70-72°C 1 H-NMR(δ ppm, CDCl 3 ) 7.49-7.51(m, 1H), 7.09-7.33(m, 8H), 6.78(s, 2H), 5.61(s, 1H), 5.06(s, 1H), 3.50(s, 2H), 3.22(t, J=5Hz, 4H), 2.80(s, 4H), 2.39(t, J=5Hz, 4H), 1.33(s, 18H) IR(cm -1 ) 3636, 3310, 2952, 1635, 1516, 1435, 1234, 1001, 754 Example 115 4-Benzyl-1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]piperidine The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-benzylpiperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.52(d, J=8Hz, 1H), 7.06-7.32(m, 8H), 6.79(s, 2H), 5.67(s, 1H), 5.06(s, 1H), 3.68-3.76(m, 2H), 2.81(s, 4H), 2.62-2.72(m, 2H), 2.53(t, J=7Hz, 4H), 1.50-1.73(m, 3H), 1.35(s, 18H), 1.10-1.23(m, 2H) IR(cm -1 ) 3645, 3440, 3330, 2960, 2925, 1645, 1525, 1455, 1440, 1250, 755, 705 Example 116 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-1,2,3,4-tetrahydroquinoline The title compound was prepared in a similar manner to that mentioned in Example 11, using 1,2,3,4-tetrahydroquinoline instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.82(d, J=7Hz, 1H), 7.36(d, J=7Hz, 1H), 7.13-7.21(m, 2H), 7.16(d, J=7Hz, 1H), 6.99-7.09(m, 3H), 6.89(bs, 1H), 6.82(s, 2H), 5.06(s, 1H), 3.80(t, J=6Hz, 2H), 2.78(t, J=6Hz, 2H), 2.69(s, 4H), 1.98(m, 2H), 1.39(s, 18H) IR(cm -1 ) 3630, 3434, 2946, 1671, 1524, 1492, 1435, 1304, 1236, 753 Example 117 2-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-1,2,3,4-tetrahydroisoquinoline The title compound was prepared in a similar manner to that mentioned in Example 11, using 1,2,3,4-tetrahydroisoquinoline instead of decylamine. m.p. 148-150°C 1 H-NMR(δ ppm, CDCl 3 ) 7.55(d, J=8Hz, 1H), 7.10-7.26(m, 7H), 6.83(s, 1H), 5.73(bs, 1H), 5.10(s, 1H), 4.52(s, 2H), 3.44(t, J=6Hz, 2H), 2.86(t, J=6Hz, 2H), 2.84(s, 4H), 1.36(s, 18H) IR(cm -1 ) 3628, 3312, 1630, 1515, 1459, 1437, 1373, 1231, 747 Example 118 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-4-(3,4-methylenedioxybenzyl)piperazine The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-(3,4-methylenedioxybenzyl)piperazine instead of decylamine. m.p. 149-151°C 1 H-NMR(δ ppm, CDCl 3 ) 7.50(d, J=7Hz, 1H), 7.18-7.23(m, 2H), 7.11(dd, J=7, 7Hz, 1H), 6.83(s, 1H), 6.70-6.76(m, 2H), 5.95(s, 2H), 5.61(bs, 1H), 5.06(s, 1H), 3.40(s, 2H), 3.22(t, J=5Hz, 4H), 2.80(s, 4H), 2.36(t, J=5Hz, 4H), 1.34(s, 18H) IR(cm -1 ) 3626, 3302, 2956, 1632, 1504, 1491, 1438, 1247, 1040, 999, 759 Example 119 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]indoline The title compound was prepared in a similar manner to that mentioned in Example 11, using indoline instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.91(d, J=8Hz, 1H), 7.61(d, J=8Hz, 1H), 7.10-7.30(m, 2H), 6.91(dd, J=8, 8Hz, 2H), 6.81(d, J=8Hz, 2H), 6.78(s, 2H), 5.65(bs, 1H), 5.10(s, 1H), 3.57(t, J=8Hz, 2H), 3.14(t, J=8Hz, 2H), 2.86(s, 4H), 1.35(s, 18H) IR(cm -1 ) 3622, 3272, 2952, 1654, 1594, 1507, 1485, 1448, 1347, 1234, 753 Example 120 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-4-methylpiperazine The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-methylpiperazine instead of decylamine. m.p. 134-137°C 1 H-NMR(δ ppm, CDCl 3 ) 7.47(d, J=8Hz, 1H), 7.17-7.26(m, 2H), 7.12(ddd, J=7, 7, 2Hz, 1H), 6.79(s, 2H), 5.56(s, 1H), 5.10(s, 1H), 3.25(t, J=5Hz, 4H), 2.82(s, 4H), 2.35(t, J=5Hz, 4H), 2.29(s, 3H), 1.37(s, 18H) IR(cm -1 ) 3632, 3440, 2940, 1636, 1511, 1437, 1002, 750 Example 121 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]perhydroazepine The title compound was prepared in a similar manner to that mentioned in Example 11, using hexamethyleneimine instead of decylamine. m.p. 136-138°C 1 H-NMR(δ ppm, CDCl 3 ) 7.67(dd, J=7, 2Hz, 1H), 7.17-7.24(m, 2H), 7.08(ddd, J=7, 7, 2Hz, 1H), 6.82(s, 2H), 5.78(s, 1H), 5.08(s, 1H), 3.26-3.34(m, 4H), 2.82(bs, 1H), 1.66-1.74(m, 4H), 1.52-1.59(m, 4H), 1.37(s, 18H) IR(cm -1 ) 3460, 1660, 1587, 1525, 1453, 1436, 755 Example 122 4-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]morpholine The title compound was prepared in a similar manner to that mentioned in Example 11, using morpholine instead of decylamine. m.p. 186-189°C 1 H-NMR(δ ppm, CDCl 3 ) 7.47(dd, J=8, 2Hz, 1H), 7.19-7.27(m, 2H), 7.14(ddd, J=7, 7, 2Hz, 1H), 6.78(s, 2H), 5.52(s, 1H), 5.09(s, 1H), 3.64(t, J=5Hz, 4H), 3.19(t, J=5Hz, 4H), 2.82(s, 4H), 1.36(s, 18H) IR(cm -1 ) 3644, 3420, 3290, 2956, 1631, 1525, 1435, 1262, 1118, 756 Example 123 3-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-3-azabicyclo[3.2.2]nonane The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-azabicyclo[3.2.2]nonane instead of decylamine. m.p. 184-186°C 1 H-NMR(δ ppm, CDCl 3 ) 7.52(d, J=8Hz, 1H), 7.26-7.34(m, 2H), 7.09(dd, J=7, 7Hz, 1H), 6.81(s, 2H), 5.71(s, 1H), 5.08(s, 1H), 3.40(d, J=4Hz, 4H), 2.82(s, 4H), 1.96-2.04(m, 2H), 1.57-1.72(m, 8H), 1.37(s, 18H) IR(cm -1 ) 3630, 3430, 3334, 2930, 2860, 1627, 1511, 754 Example 124 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-4-phenylpiperazine The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-phenylpiperazine instead of decylamine. m.p. 155-156°C 1 H-NMR(δ ppm, CDCl 3 ) 7.11-7.48(m, 6H), 6.88-6.92(m, 1H), 6.89(d, J=8Hz, 2H), 6.79(s, 2H), 5.61(t, J=5Hz, 4H), 3.12(t, J=5Hz, 4H), 2.83(s, 4H), 1.37(s, 18H) IR(cm -1 ) 3584, 3372, 2960, 1639, 1601, 1505, 1435, 1234, 999, 753 Example 125 8-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-1,4-dioxa-8-azaspiro[4.5]decane The title compound was prepared in a similar manner to that mentioned in Example 11, using 1,4-dioxa-8-azaspiro[4.5]decane instead of decylamine. m.p. 163-164°C 1 H-NMR(δ ppm, CDCl 3 ) 7.45(d, J=7Hz, 1H), 7.17-7.26(m, 2H), 7.12(dd, J=7, 7Hz, 1H), 6.78(s, 2H), 5.59(bs, 1H), 5.09(s, 1H), 3.96(s, 4H), 3.30(t, J=6Hz, 4H), 2.82(s, 4H), 1.65(t, J=6Hz, 4H), 1.36(s, 18H) IR(cm -1 ) 3430, 3300, 2955, 1645, 1510, 1490, 1455, 1440, 1250, 1120, 950, 750 Example 126 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-4-(1-pyrrolidinylcarbonylmethyl)piperazine The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-(1-pyrrolidinylcarbonylmethyl)piperazine instead of decylamine. m.p. 212-214°C 1 H-NMR(δ ppm, CDCl 3 ) 7.47(d, J=8Hz, 1H), 7.16-7.25(m, 2H), 7.11(ddd, J=7, 7, 1Hz, 1H), 6.78(s, 2H), 5.59(s, 1H), 5.10(s, 1H), 3.45-3.52(m, 4H), 3.28(t, J=5Hz, 4H), 3.11(s, 2H), 2.81(s, 4H), 2.50(t, J=5Hz, 4H), 1.80-2.00(m, 4H), 1.36(s, 18H) IR(cm -1 ) 3500, 3328, 2960, 1626, 1521, 1457, 1437, 750 Example 127 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-4-piperidinopiperidine The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-piperidinopiperidine instead of decylamine. m.p. 64-67°C 1 H-NMR(δ ppm, CDCl 3 ) 7.48(d, J=7Hz, 1H), 7.16-7.25(m, 2H), 7.11(ddd, J=7, 7, 2Hz, 1H), 6.79(s, 2H), 5.62(s, 1H), 5.09(s, 1H), 3.73-3.81(m, 2H), 2.81(s, 4H), 2.65-2.75(m, 2H), 2.44-2.51(m, 4H), 2.33-2.44(m, 1H), 1.75-1.82(m, 2H), 1.54-1.62(m, 4H), 1.39-1.50(m, 4H), 1.37(s, 18H) IR(cm -1 ) 3636, 3420, 2934, 1640, 1520, 1450, 1250, 750 Example 128 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-4-(p-toluenesulfonyl)piperazine The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-(p-toluenesulfonyl)piperazine instead of decylamine. m.p. 195-197°C 1 H-NMR(δ ppm, CDCl 3 ) 7.61(d, J=8Hz, 2H), 7.29-7.36(m, 3H), 7.19-7.24(m, 3H), 6.73(s, 2H), 5.41(bs, 1H), 5.12(s, 1H), 3.26(t, J=5Hz, 4H), 2.93(t, J=5Hz, 4H), 2.70-2.83(m, 4H), 2.45(s, 3H), 1.35(s, 18H) IR(cm -1 ) 3630, 3410, 2950, 1635, 1625, 1350, 1170, 730 Example 129 1-Benzoyl-4-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]piperazine The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-benzoylpiperazine instead of decylamine. m.p. 207-209°C 1 H-NMR(δ ppm, CDCl 3 ) 7.37-7.48(m, 6H), 7.12-7.27(m, 3H), 6.76(s, 2H), 5.52(bs, 1H), 5.08(s, 1H), 3.12-3.85(m, 8H), 2.82(s, 4H), 1.33(s, 18H) IR(cm -1 ) 3570, 3266, 2950, 1629, 1530, 1435, 1260, 1007, 754 Example 130 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]decahydroquinoline The title compound was prepared in a similar manner to that mentioned in Example 11, using decahydroquinoline instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.57(d, J=8Hz, 1H), 7.12-7.21(m, 2H), 7.07(dd, J=7, 7Hz, 1H), 6.86(s, 2H), 5.88(bs, 1H), 5.08(s, 1H), 4.06(m, 1H), 3.45(m, 1H), 2.75-2.90(m, 5H), 1.90(m, 1H), 1.63-1.80(m, 4H), 1.20-1.60(m, 8H), 1.39(m, 18H) IR(cm -1 ) 3430, 2924, 1632, 1510, 1434, 750 Example 131 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-4-pentanoylpiperazine The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-pentanoylpiperazine instead of decylamine. m.p. 126-128°C 1 H-NMR(δ ppm, CDCl 3 ) 7.44(d, J=9Hz, 1H), 7.12-7.27(m, 3H), 6.77(s, 2H), 5.52(bs, 1H), 5.12(s, 1H), 3.56-3.63(m, 2H), 3.40-3.46(m, 2H), 3.27-3.34(m, 2H), 3.08-3.14(m, 2H), 2.82(s, 4H), 2.30(t, J=5Hz, 2H), 1.58-1.67(m, 2H), 1.36(s, 18H), 1.28-1.38(m, 4H) IR(cm -1 ) 3300, 2952, 1636, 1530, 1435, 1240, 994, 755 Example 132 1-[N-[2-(3,5-di-tert-butyl-4-hydroxystyryl)phenyl]carbamoyl]-4-methylpiperazine The title compound was prepared in a similar manner to that mentioned in Example 101, using 1-methylpiperazine instead of 2-(aminomethyl)pyridine. m.p. 192-194°C 1 H-NMR(δ ppm, CDCl 3 ) 7.65(d, J=8Hz, 1H), 7.46-7.50(m, 1H), 7.33(s, 2H), 7.20-7.26(m, 1H), 7.11(dd, J=9, 1Hz, 1H), 6.99(d, J=16Hz, 1H), 6.94(d, J=16Hz, 1H), 6.39(bs, 1H), 5.34(s, 1H), 3.51(t, J=5Hz, 4H), 2.43(t, J=5Hz, 4H), 2.32(m, 3H), 1.47(s, 18H) IR(cm -1 ) 3636, 3420, 3288, 2952, 1635, 1525, 1485, 1439, 1236, 1149, 959, 765, 755 Example 133 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-4-nicotinoylpiperazine The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-nicotinoylpiperazine instead of decylamine. m.p. 171-172°C 1 H-NMR(δ ppm, CDCl 3 ) 8.70(dd, J=5, 2Hz, 1H), 8.66(d, J=1Hz, 1H), 7.75(ddd, J=8, 8, 2Hz, 1H), 7.36-7.42(m, 2H), 7.14-7.27(m, 3H), 6.75(s, 2H), 5.52(s, 1H), 5.11(s, 1H), 3.10-3.80(m, 8H), 2.82(s, 4H), 1.33(s, 18) IR(cm -1 ) 3636, 3420, 3288, 2952, 1635, 1525, 1485, 1439, 1236, 1149, 959, 765, 755 Example 134 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-cyclohexyl-4-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-cyclohexylpiperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.15-7.25(m, 4H), 6.79(s, 2H), 5.38(bs, 2H), 5.12(s, 1H), 4.55(bs, 1H), 3.65-3.75(m, 1H), 2.90-2.98(m, 2H), 2.75-2.90(m, 4H), 2.35-2.45(m, 3H), 1.85-2.00(m, 4H), 1.78(bs, 2H), 1.45-1.65(m, 3H), 1.38(s, 18H), 1.00-1.35(m, 5H) IR(cm -1 ) 3638, 3262, 1658, 1643, 1560, 1542, 1435, 1233, 754 Example 135 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(3-morpholinopropyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-(3-aminopropyl)morpholine instead of decylamine. m.p. 138-139°C 1 H-NMR(δ ppm, CDCl 3 ) 7.19-7.29(m, 4H), 6.80(s, 2H), 5.19(bs, 1H), 5.12(s, 1H), 5.04(t, J=5Hz, 1H), 3.44(bs, 4H), 3.25(q, J=6Hz, 2H), 2.77-2.87(m, 4H), 2.25-2.35(m, 6H), 1.60(quint., J=7Hz, 2H), 1.38(s, 18H) IR(cm -1 ) 3528, 3304, 1633, 1565, 1436, 1238, 1116, 872, 752 Example 136 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(2-morpholinoethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-(2-aminoethyl)morpholine instead of decylamine. m.p. 166-167°C 1 H-NMR(δ ppm, CDCl 3 ) 7.19-7.28(m, 4H), 6.80(s, 2H), 5.19(s, 1H), 5.14(s, 1H), 4.91(s, 1H), 3.56(t, J=6Hz, 4H), 3.24(t, J=6Hz, 2H), 2.75-2.89(m, 4H), 2.30-2.42(m, 6H), 1.38(s, 18H) IR(cm -1 ) 3566, 3326, 1643, 1574, 1436, 1300, 1238, 1116, 755 Example 137 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[3-(2-methyl-1-piperidyl)propyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-(3-aminopropyl)-2-methylpiperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.14-7.30(m, 4H), 6.81(s, 2H), 5.43(bs, 1H), 5.36(bs, 1H), 5.11(s, 1H), 3.15-3.30(m, 2H), 2.70-2.87(m, 6H), 2.20-2.30(m, 2H), 2.01(t, J=10Hz, 1H), 1.40-1.65(m, 5H), 1.38(s, 18H), 1.00-1.40(m, 3H), 0.98(d, J=6Hz, 3H) IR(cm -1 ) 3638, 3294, 1643, 1543, 1436, 1234, 754 Example 138 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[2-(1-pyrrolidinyl)ethyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-(2-aminoethyl)pyrrolidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.37(d, J=7Hz, 1H), 7.11-7.21(m, 3H), 6.82(s, 2H), 5.55(bs, 1H), 5.26(s, 1H), 5.03(s, 1H), 3.29(t, J=6Hz, 2H), 2.65-2.85(m, 5H), 2.59(t, J=6Hz, 2H), 2.53(bs, 3H), 1.74(bs, 4H), 1.38(s, 18H) IR(cm -1 ) 3638, 3350, 1686, 1546, 1436, 1234, 753 Example 139 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(2-propyl)-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(2-propyl)piperidine instead of decylamine. m.p. 191-193°C 1 H-NMR(δ ppm, CDCl 3 ) 7.15-7.26(m, 4H), 6.78(s, 2H), 5.11(bs, 2H), 4.30(bs, 1H), 3.59-3.72(m, 1H), 2.73-2.90(m, 7H), 2.25-2.37(m, 2H), 1.87-1.98(m, 2H), 1.30-1.50(m, 2H), 1.38(s, 18H), 1.07(d, J=6Hz, 6H) IR(cm -1 ) 3358, 2948, 1641, 1561, 1435, 1235 Example 140 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[2-(4-fluorophenyl)-2-methylpropyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-fluoro-β,β-dimethylphenethylamine instead of decylamine. m.p. 179-180°C 1 H-NMR(δ ppm, CDCl 3 ) 7.14-7.20(m, 4H), 7.08(t, J=7Hz, 1H), 6.87-6.96(m, 3H), 6.74(s, 2H), 5.08(s, 1H), 5.00(s, 1H), 3.95-4.05(m, 1H), 3.30(d, J=6Hz, 2H), 2.70-2.80(m, 4H), 1.36(s, 18H), 1.24(s, 6H) IR(cm -1 ) 3638, 3370, 1644, 1653, 1613, 1436, 1231, 1166, 833, 762 Example 141 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[2-[4-(1-pyrrolidinyl)phenyl]-2-methylpropyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-[4-(1-amino-2-methyl-2-propyl)phenyl]pyrrolidine instead of decylamine. m.p. 195-196°C 1 H-NMR(δ ppm, CDCl 3 ) 7.02-7.18(m, 6H), 6.77(s, 2H), 6.43(d, J=9Hz, 2H), 5.08(s, 2H), 4.14(t, J=6Hz, 1H), 3.28(t, J=6Hz, 2H), 3.22-3.25(m, 4H), 2.70-2.78(m, 4H), 1.97-2.01(m, 4H), 1.37(s, 18H), 1.23(s, 6H) IR(cm -1 ) 3642, 3354, 1642, 1615, 1562, 1524, 1369, 1234, 814, 750 Example 142 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-benzyl-3-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-amino-1-benzylpiperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.20-7.40(m, 9H), 6.79(s, 2H), 5.12(bs, 1H), 5.09(s, 1H), 3.87-3.96(m, 1H), 3.49(bs, 1H), 3.37(d, J=13Hz, 1H), 3.28(d, J=13Hz, 1H), 2.70-2.90(m, 4H), 2.40-2.50(m, 2H), 1.30-1.70(m, 24H) IR(cm -1 ) 3632, 3338, 2948, 1639, 1542, 1435, 1234, 744, 699 Example 143 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[2-(2-fluorophenyl)-2-methylpropyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 2-fluoro-β,β-dimethylphenethylamine instead of decylamine. m.p. 182-183°C 1 H-NMR(δ ppm, CDCl 3 ) 6.88-7.21(m, 8H), 6.75(s, 2H), 5.07(s, 1H), 5.02(s, 1H), 4.02-4.09(m, 1H), 3.50(d, J=6Hz, 2H), 2.67-2.78(m, 4H), 1.36(s, 18H), 1.33(s, 6H) IR(cm -1 ) 3650, 3330, 2960, 1640, 1575, 1445, 1255, 765 Example 144 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[2-(3-fluorophenyl)-2-methylpropyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-fluoro-β,β-dimethylphenethylamine instead of decylamine. m.p. 165-166°C 1 H-NMR(δ ppm, CDCl 3 ) 7.04-7.23(m, 4H), 6.80-7.00(m, 4H), 6.74(s, 2H), 5.08(s, 1H), 4.94(s, 1H), 3.98(t, J=6Hz, 1H), 3.32(d, J=6Hz, 2H), 2.68-2.79(m, 4H), 1.36(s, 18H), 1.25(s, 6H) IR(cm -1 ) 3640, 3350, 2970, 1645, 1615, 1590, 1560, 1440, 910, 765, 700 Example 145 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-benzyl-4-piperidyl)-N'-ethylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-ethylamino-1-benzylpiperidine instead of decylamine. m.p. 149-151°C 1 H-NMR(δ ppm, CDCl 3 ) 7.72(d, J=8Hz, 1H), 7.15-7.33(m, 7H), 7.07(t, J=7Hz, 1H), 6.83(s, 2H), 5.91(bs, 1H), 5.07(s, 1H), 4.16-4.38(m, 1H), 3.48(s, 2H), 3.02(q, J=7Hz, 2H), 2.93(d, J=12Hz, 2H), 2.82(bs, 4H), 2.03-2.10(m, 2H), 1.60-1.75(m, 4H), 1.37(s, 18H), 1.16(t, J=7Hz, 3H) IR(cm -1 ) 3334, 2954, 1631, 1520, 1502, 1263, 1202, 743 Example 146 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-benzyl-4-piperidyl)-N'-propylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-benzyl-4-propylaminopiperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.76(d, J=7Hz, 1H), 7.10-7.35(m, 7H), 7.04(td, J=6, 1Hz, 1H), 6.87(s, 2H), 6.07(bs, 1H), 5.06(s, 1H), 4.12-4.23(m, 1H), 3.48(s, 2H), 3.04(bt, J=8Hz, 2H), 2.94(d, J=12Hz, 2H), 2.81(s, 4H), 2.00-2.10(m, 2H), 1.50-1.75(m, 6H), 1.39(s, 18H), 0.86(t, J=7Hz, 3H) IR(cm -1 ) 3634, 3450, 2956, 1650, 1509, 1451, 1234, 742 Example 147 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-benzyl-4-piperidyl)-N'-(2-propyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-benzyl-4-[(2-propyl)amino]piperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.65(d, J=8Hz, 1H), 7.10-7.30(m, 7H), 7.04(td, J=7, 1Hz, 1H), 6.89(s, 2H), 6.03(bs, 1H), 5.05(s, 1H), 3.70-3.90(m, 2H), 3.47(s, 2H), 2.75-2.98(m, 6H), 1.90-2.05(m, 4H), 1.55-1.70(m, 2H), 1.39(s, 18H), 1.31(d, J=7Hz, 6H) IR(cm -1 ) 3450, 2954, 1650, 1521, 1451, 1237, 744 Example 148 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(2-fluorobenzyl)-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(2-fluorobenzyl)piperidine instead of decylamine. m.p. 136-137°C 1 H-NMR(δ ppm, CDCl 3 ) 7.14-7.34(m, 6H), 6.95-7.10(m, 2H), 6.77(s, 2H), 5.10(s, 1H), 4.99(s, 1H), 4.10(d, J=8Hz, 1H), 3.55-3.71(m, 1H), 3.52(s, 2H), 2.68-2.88(m, 6H), 2.07-2.17(m, 2H), 1.82-1.90(m, 2H), 1.37(s, 18H), 1.24-1.35(m, 2H) IR(cm -1 ) 3640, 3340, 2960, 1650, 1590, 1570, 1495, 1235, 765 Example 149 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(3-fluorobenzyl)-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(3-fluorobenzyl)piperidine instead of decylamine. m.p. 99-100°C 1 H-NMR(δ ppm, CDCl 3 ) 7.15-7.27(m, 5H), 7.67-7.04(m, 2H), 6.86-6.94(m, 1H), 5.10(s, 1H), 4.12(d, J=8Hz, 1H), 3.57-3.70(m, 1H), 3.42(s, 2H), 2.66-2.86(m, 6H), 2.06(t, J=12Hz, 2H), 1.86(d, J=12Hz, 2H), 1.38(s, 18H), 1.24-1.35(m, 2H) IR(cm -1 ) 3635, 3340, 2950, 1640, 1590, 1565, 1490, 1440, 1235, 880, 750, 690 Example 150 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(4-chlorobenzyl)-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(4-chlorobenzyl)piperidine instead of decylamine. m.p. 184-185°C 1 H-NMR(δ ppm, CDCl 3 ) 7.15-7.32(m, 8H), 6.77(s, 2H), 5.10(s, 1H), 4.98(s, 1H), 4.09(d, J=8Hz, 1H), 3.57-3.70(m, 1H), 3.39(s, 2H), 2.74-2.87(m, 4H), 2.69(d, J=11Hz, 2H), 2.04(t, J=11Hz, 2H), 1.81-1.88(m, 2H), 1.37(s, 18H), 1.14-1.22(m, 2H) IR(cm -1 ) 3645, 3360, 2940, 1640, 1590, 1555, 1490, 1435, 1295, 1235, 1095, 750 Example 151 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(3,4-difluorobenzyl)-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(3,4-difluorobenzyl)piperidine instead of decylamine. m.p. 155-156°C 1 H-NMR(δ ppm, CDCl 3 ) 6.92-7.28(m, 7H), 6.77(s, 2H), 5.10(s, 1H), 4.97(s, 1H), 4.08(d, J=8Hz, 1H), 3.58-3.72(m, 1H), 3.37(s, 2H), 2.74-2.87(m, 4H), 2.05(t, J=11Hz, 2H), 1.82-1.90(m, 2H), 1.38(s, 18H), 1.24-1.35(m, 2H) IR(cm -1 ) 3650, 3370, 2965, 1645, 1570, 1525, 1440, 1295, 1240, 885, 785, 765 Example 152 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl)-N'-[1-(4-fluorophenethyl)-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(4-fluorophenethyl)piperidine instead of decylamine. m.p. 117-119°C 1 H-NMR(δ ppm, CDCl 3 ) 7.10-7.20(m, 6H), 6.94(td, J=7, 2Hz, 2H), 6.78(s, 2H), 5.11(s, 1H), 5.04(bs, 1H), 4.13(bd, J=8Hz, 1H), 3.58-3.70(m, 1H), 2.70-2.90(m, 8H), 2.45-2.55(m, 2H), 2.08-2.12(m, 2H), 1.85-1.95(m, 2H), 1.30-1.40(m, 2H), 1.38(s, 18H) IR(cm -1 ) 3630, 3314, 2948, 1634, 1565, 1510, 1228, 748 Example 153 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(3,5-difluorobenzyl)-4-piperidyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-amino-1-(3,5-difluorobenzyl)piperidine instead of decylamine. m.p. 119-120°C 1 H-NMR(δ ppm, CDCl 3 ) 7.17-7.28(m, 4H), 6.82(d, J=6Hz, 2H), 6.77(s, 2H), 6.62-6.69(m, 1H), 5.11(s, 1H), 4.97(s, 1H), 4.09(d, J=8Hz, 1H), 3.58-3.71(m, 1H), 3.40(s, 2H), 2.66-2.88(m, 6H), 2.07(t, J=11Hz, 2H), 1.83-1.92(m, 2H), 1.38(s, 18H), 1.25-1.36(m, 2H) IR(cm -1 ) 3640, 3350, 2960, 1635, 1605, 1505, 1440, 1325, 1235, 1120, 995, 855 Example 154 2-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-cis-decahydroquinoline The title compound was prepared in a similar manner to that mentioned in Example 11, using cis-decahydroquinoline instead of decylamine. m.p. 132-133°C 1 H-NMR(δ ppm, CDCl 3 ) 7.64(d, J=8Hz, 1H), 7.23-7.30(m, 2H), 7.11(t, J=7Hz, 1H), 6.93(s, 2H), 5.94(s, 1H), 5.14(s, 1H), 4.09-4.20(m, 1H), 3.48-3.59(m, 1H), 2.83-2.94(m, 5H), 1.50-2.00(m, 9H), 1.45(s, 18H), 1.24-1.42(m, 4H) IR(cm -1 ) 3640, 3320, 2925, 2860, 1630, 1515, 1435, 1360, 1275, 1235, 1160, 755 Example 155 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-3-fluorophenyl]-N'-(1-benzyl-4-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 108, using 4-(2-amino-6-fluorophenethyl)-2,6-di-tert-butylphenol instead of 4-(2-amino-3,5-difluorophenethyl)-2,6-di-tert-butylphenol. m.p. 103-105°C 1 H-NMR(δ ppm, CDCl 3 ) 7.20-7.35(m, 5H), 7.13(t, J=8Hz, 1H), 7.03(d, J=8Hz, 1H), 6.93(t, J=9Hz, 1H), 6.75(s, 2H), 5.13(s, 1H), 4.60(bs, 1H), 3.95(bd, J=8Hz, 1H), 3.54-3.66(m, 1H), 3.44(s, 2H), 2.70-2.90(m, 6H), 2.00-2.10(m, 2H), 1.80-1.90(m, 2H), 1.30-1.40(m, 2H), 1.36(s, 18H) IR(cm -1 ) 3630, 3300, 2948, 1632, 1565, 1452, 1235, 699 Example 156 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[1-(4-fluorobenzyl)-4-piperidyl]-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-(4-fluorobenzyl)-4-(methylamino)piperidine instead of decylamine. m.p. 177-178°C 1 H-NMR(δ ppm, CDCl 3 ) 7.63(d, J=8Hz, 1H), 7.17-7.28(m, 4H), 7.08-7.13(m, 1H), 6.95-7.03(m, 2H), 6.78(s, 2H), 5.61(s, 1H), 5.08(s, 1H), 4.17-4.28(m, 1H), 3.43(s, 2H), 2.90(d, J=12Hz, 2H), 2.81(s, 4H), 2.50(s, 3H), 1.98-2.07(m, 2H), 1.54-1.68(m, 4H), 1.35(s, 18H) IR(cm -1 ) 3630, 3330, 2970, 1635, 1520, 1440, 1330, 1230, 1050, 760, Example 157 N-[2-(3,5-di-tert-butyl-4-hydroxystyryl)phenyl]-N'-[1-(4-fluorobenzyl)-4-piperidyl]-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 101, using 1-(4-fluorobenzyl)-4-(methylamino)piperidine instead of 2-(aminomethyl)pyridine. m.p. 174-175°C 1 H-NMR(δ ppm, CDCl 3 ) 7.79(d, J=8Hz, 1H), 7.45(dd, J=7, 1Hz, 1H), 7.31(s, 2H), 7.20-7.30(m, 3H), 7.05-7.13(m, 1H), 6.93-7.03(m, 4H), 6.38(s, 1H), 5.32(s, 1H), 4.14-4.26(m, 1H), 3.46(s, 2H), 2.85-2.96(m, 5H), 1.99-2.10(m, 2H), 1.63-1.82(m, 4H), 1.46(s, 18H) IR(cm -1 ) 3640, 3450, 2960, 1640, 1510, 1225, 1160, 1045, 965, 760 Example 158 N-[2-(3,5-di-tert-butyl-4-hydroxystyryl)phenyl]-N'-(1-benzyl-4-piperidyl)-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 101, using 1-benzyl-4-(methylamino)piperidine instead of 2-(aminomethyl)pyridine. m.p. 163-164°C 1 H-NMR(δ ppm, CDCl 3 ) 7.78(d, J=7Hz, 1H), 7.45(dd, J=8, 1Hz, 1H), 7.20-7.35(m, 8H), 7.04-7.12(m, 1H), 7.00(d, J=16Hz, 1H), 6.93(d, J=16Hz, 1H), 6.38(s, 1H), 5.32(s, 1H), 4.14-4.27(m, 1H), 3.48(s, 2H), 2.94(d, J=12Hz, 2H), 2.90(s, 3H), 2.00-2.11(m, 2H), 1.60-1.84(m, 4H), 1.46(s, 18H) IR(cm -1 ) 3625, 3440, 3260, 2960, 1635, 1530, 1485, 1240, 1150, 1045, 960, 755, 745, 700 Example 159 2-[N-[2-(3,5-di-tert-butyl-4-hydroxystyryl)phenyl]carbamoyl]-cis-decahydroquinoline The title compound was prepared in a similar manner to that mentioned in Example 101, using cis-decahydroquinoline instead of 2-(aminomethyl)pyridine. 1 H-NMR(δ ppm, CDCl 3 ) 7.71(d, J=8Hz, 1H), 7.46(d, J=6Hz, 1H), 7.33(s, 2H), 7.20-7.28(m, 1H), 7.05-7.11(m, 1H), 7.00(d, J=16Hz, 1H), 6.93(d, J=16Hz, 1H), 6.41(s, 1H), 5.32(s, 1H), 3.85-4.07(m, 2H), 1.68-1.97(m, 5H), 1.47-1.64(m, 5H), 1.47(s, 18H), 1.18-1.43(m, 3H) IR(cm -1 ) 3640, 3450, 3300, 2930, 2870, 1645, 1525, 1445, 1240, 1160, 965, 755 Example 160 N-[4-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(1-benzyl-4-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-(4-aminophenethyl)-2,6-di-tert-butylphenol instead of 4-(2-aminophenethyl)-2,6-di-tert-butylphenol and using 4-amino-1-benzylpiperidine instead of decylamine. m.p. 195-197°C 1 H-NMR(δ ppm, CDCl 3 ) 7.22-7.34(m, 5H), 7.15(s, 4H), 6.92(s, 2H), 6.10(s, 1H), 5.06(s, 1H), 4.56(d, J=8Hz, 1H), 3.66-3.78(m, 1H), 3.49(s, 2H), 2.75-2.90(m, 6H), 2.07-2.18(m, 2H), 1.91-1.99(m, 2H), 1.36-1.47(m, 2H), 1.43(s, 18H) IR(cm -1 ) 3620, 3378, 2946, 1659, 1604, 1542, 1515, 1435, 1324, 1234, 740 Example 161 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-allylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using allylamine instead of decylamine. m.p. 169-172°C 1 H-NMR(δ ppm, CDCl 3 ) 7.16-7.32(m, 5H), 6.78(s, 2H), 5.73-5.85(m, 1H), 4.96-5.14(m, 3H), 4.20-4.26(m, 1H), 3.73-3.80(m, 2H), 2.76-2.90(m, 4H), 1.37(s, 18H) IR(cm -1 ) 3632, 3334, 2956, 1653, 1587, 1570, 1561, 1436, 1235, 924, 769 Example 162 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-nitrophenethyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-nitrophenethylamine instead of decylamine. m.p. 134-136°C 1 H-NMR(δ ppm, CDCl 3 ) 8.08(d, J=8Hz, 1H), 7.10-7.29(m, 6H), 6.75(s, 2H), 5.12(s, 1H), 5.05(s, 1H), 4.28(t, J=6Hz, 1H), 3.39(td, J=7, 6Hz, 2H), 2.73-2.90(m, 6H), 1.35(s, 18H) IR(cm -1 ) 3630, 3314, 2954, 1639, 1561, 1519, 1436, 1347, 753 Example 163 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-6-methoxyphenyl]-N'-(1-benzyl-4-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 108, using 4-(2-amino-3-methoxyphenethyl)-2,6-di-tert-butylphenol instead of 4-(2-amino-3,5-difluorophenethyl)-2,6-di-tert-butylphenol m.p. 184-185°C 1 H-NMR(δ ppm, CDCl 3 ) 7.20-7.30(m, 6H), 6.88(d, J=8Hz, 1H), 6.80(s, 2H), 6.77(d, J=8Hz, 1H), 5.07(s, 1H), 4.88(s, 1H), 4.09(d, J=8Hz, 1H), 3.76(s, 3H), 3.60-3.70(m, 1H), 3.43(s, 2H), 2.86-2.90(m, 2H), 2.70-2.77(m, 4H), 2.05(t, J=11Hz, 2H), 1.86(d, J=10Hz, 2H), 1.38(s, 18H), 1.25(q, J=10Hz, 2H) IR(cm -1 ) 3638, 3308, 1653, 1589, 1563, 1556, 1468, 1454, 1435, 1260, 1232, 738 Example 164 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-[endo-9-(4-fluorobenzyl)-3-oxa-9-azabicyclo[3.3.1]non-7-yl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using endo-7-amino-9-(4-fluorobenzyl)-3-oxa-9-azabicyclo[3.3.1]nonane instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.18-7.29(m, 6H), 7.06(d, J=11Hz, 1H), 6.99(d, J=9Hz, 1H), 6.96(d, J=9Hz, 1H), 6.83(s, 2H), 5.22(s, 1H), 5.09(s, 1H), 4.37(dd, J=17, 7Hz, 1H), 3.73(d, J=15Hz, 2H), 3.71(s, 2H), 3.39(d, J=11Hz, 2H), 2.84-2.87(m, 2H), 2.76-2.79(m, 2H), 2.52(s, 2H), 2.30-2.37(m, 2H), 1.39(s, 18H), 1.31-1.40(m, 2H) IR(cm -1 ) 3636, 3324, 1652, 1525, 1511, 1506, 1436, 1223, 787, 759 Example 165 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-(1-benzyl-4-piperidyl)-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 108, using 1-benzyl-4-(methylamino)piperidine instead of 4-amino-1-benzylpiperidine. m.p. 187-191°C 1 H-NMR(δ ppm, CDCl 3 ) 7.20-7.40(m, 5H), 6.70-6.80(m, 4H), 5.09(s, 1H), 4.91(bs, 1H), 4.10-4.23(m, 1H), 3.47(s, 2H), 2.90-3.00(m, 2H), 2.80-2.90(m, 4H), 2.58(s, 3H), 2.00-2.10(m, 2H), 1.60-1.80(m, 4H), 1.36(s, 18H) IR(cm -1 ) 3616, 3312, 1638, 1510, 1436, 1323, 1118 Example 166 2-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]carbamoyl]-cis-decahydroquinoline The title compound was prepared in a similar manner to that mentioned in Example 108, using cis-decahydroquinoline instead of 4-amino-1-benzylpiperidine. m.p. 83-85°C 1 H-NMR(δ ppm, CDCl 3 ) 6.83(s, 2H), 6.70-6.80(m, 2H), 5.26(bs, 1H), 5.09(s, 1H), 4.05(bs, 1H), 3.49(bs, 2H), 2.70-2.90(m, 5H), 1.84-1.94(m, 1H), 1.65-1.80(m, 4H), 1.20-1.60(m, 8H), 1.39(s, 18H) IR(cm -1 ) 3588, 3316, 2924, 1713, 1638, 1511, 1435, 1120 Example 167 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-(1-benzyl-4-piperidyl)urea hydrochloride N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-(1-benzyl-4-piperidyl)urea (1.15 g) was suspended in ethanol (20 ml) and heated at 50°C to dissolve it. To the solution was added 4N hydrochloric acid/ethyl acetate solution (anhydrous)(0.5 ml). This solution was concentrated to a volume of 5 ml, cooled to 0-5°C and allowed to stand for 4 hrs. The resultant crystals were filtered and dried to afford the title compound (1.00 g, 81%). m.p. 170-175°C 1 H-NMR(δ ppm, CDCl 3 ) 12.09(bs, 1H), 7.55(d, J=6Hz, 2H), 7.30-7.40(m, 3H), 6.84(s, 2H), 6.72(d, J=8Hz, 1H), 6.65(td, J=8, 2Hz, 1H), 5.10(s, 1H), 4.12(d, J=7Hz, 1H), 3.75-3.86(m, 1H), 3.35-3.40(m, 2H), 2.65-2.85(m, 6H), 2.10-2.25(m, 4H), 1.39(s, 18H) IR(cm -1 ) 3430, 3300, 2952, 1680, 1554, 1436, 1236, 1122 Example 168 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-6-methylphenyl]-N'-(1-benzyl-4-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 108, using 4-(2-amino-3-methylphenethyl)-2,6-di-tert-butylphenol instead of 4-(2-amino-3,5-difluorophenethyl)-2,6-di-tert-butylphenol. m.p. 185-186°C 1 H-NMR(δ ppm, CDCl 3 ) 7.04-7.34(m, 8H), 6.78(s, 2H), 5.08(s, 1H), 4.83(s, 1H), 3.90(d, J=8Hz, 1H), 3.57-3.72(m, 1H), 3.42(s, 2H), 2.62-2.90(m, 6H), 2.19(s, 3H), 2.03(dd, J=12, 11Hz, 2H), 1.83(d, J=11Hz, 2H), 1.38(s, 18H), 1.16-1.32(m, 2H) IR(cm -1 ) 3638, 3324, 2950, 1639, 1555, 1436, 1233, 769, 734, 698 Example 169 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-(1-benzyl-4-piperidyl)urea methanesulfonate N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-(1-benzyl-4-piperidyl)urea (0.50 g) was suspended in ethanol (10 ml) and heated at 50°C to dissolve it. To the solution was added methanesulfonic acid (56 µl) and this solution was concentrated. The concentrate was dissolved with a mixed solvent of ethyl acetate (1 ml) and diisopropylether (3 ml). The solution was cooled to 0-5°C and allowed to stand overnight. The resultant crystals were filtered and dried to give the title compound (0.51 g, 87%). m.p. 252-254°C 1 H-NMR(δ ppm, CDCl 3 ) 10.23(bs, 1H), 7.30-7.45(m, 5H), 6.80-6.92(m, 3H), 6.57-6.68(m, 1H), 5.10(s, 1H), 4.30(bs, 1H), 4.12(bs, 1H), 3.74-3.88(m, 1H), 3.40-3.50(m, 2H), 3.20-3.32(m, 1H), 2.60-2.80(m, 9H), 1.90-2.15(m, 4H), 1.39(s, 18H) IR(cm -1 ) 3262, 2954, 1657, 1562, 1438, 1220, 1163, 1119, 1041 Example 170 (S)-N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(α-methoxycarbonyl)benzylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using (S)-α-phenylglycine methyl ester instead of decylamine. m.p. 145-150°C 1 H-NMR(δ ppm, CDCl 3 ) 7.170-7.34(m, 9H), 6.76(s, 2H), 5.51(d, J=8Hz, 1H), 5.23(d, J=7Hz, 1H), 5.13(s, 1H), 5.09(s, 1H), 3.68(s, 3H), 2.74-2.88(m, 4H), 1.35(s, 18H) IR(cm -1 ) 3644, 3345, 2944, 1752, 1644, 1546, 1436, 1211 Example 171 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(2,4-dimethyl-1,8-naphthyridin-7-yl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 7-amino-2,4-dimethyl-1,8-naphthyridine instead of decylamine. m.p. 235-237°C 1 H-NMR(δ ppm, CDCl 3 ) 8.22(d, J=9Hz, 1H), 7.86-7.96(m, 1H), 7.10-7.30(m, 3H), 7.02(s, 1H), 6.80(s, 2H), 4.93(s, 1H), 3.15-3.27(m, 2H), 2.90-3.01(m, 2H), 2.62(s, 3H), 2.56(bs, 3H), 1.23(s, 18H) IR(cm -1 ) 3636, 2952, 1687, 1615, 1599, 1560, 1527, 1403, 1307, 751 Example 172 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(bicyclo[3.3.0]-2-octyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using 1-aminobicyclo[3.3.0]octane instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.14-7.29(m, 4H), 6.80(s, 2H), 5.11(s, 1H), 5.060(s, 1H), 4.15(d, J=8Hz, 1H), 3.62-3.72(m, 1H), 2.75-2.88(m, 4H), 2.34-2.45(m, 1H), 1.87-2.01(m, 2H), 1.72-1.83(m, 1H), 1.43-1.63(m, 4H), 1.38(s, 18H), 1.07-1.31(m, 3H) IR(cm -1 ) 3634, 2948, 2864, 1637, 1563, 1434, 1231, 760 Example 173 (S)-N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(α-benzyloxycarbonyl)benzylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using (S)-α-phenylglycine benzyl ester instead of decylamine. m.p. 132-134°C 1 H-NMR(δ ppm, CDCl 3 ) 7.13-7.33(m, 14H), 6.75(s, 2H), 5.57(d, J=8Hz, 1H), 5.27(d, J=7Hz, 1H), 5.15(s, 1H), 5.11(s, 2H), 5.08(s, 1H), 2.74-2.87(m, 4H), 1.34(s, 18H) IR(cm -1 ) 3642, 3344, 2944, 1749, 1643, 1587, 1553, 1168, 749, 697 Example 174 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-2-ethylpiperidine The title compound was prepared in a similar manner to that mentioned in Example 11, using 2-ethylpiperidine instead of decylamine. m.p. 137-138°C 1 H-NMR(δ ppm, CDCl 3 ) 7.52-7.58(m, 1H), 7.16-7.23(m, 2H), 7.04-7.10(m, 1H), 6.84(s, 2H), 5.78(s, 1H), 5.08(s, 1H), 3.91-4.00(m, 1H), 3.51-3.61(m, 1H), 2.76-2.87(m, 5H), 1.45-1.80(m, 8H), 1.38(s, 18H), 0.86(t, J=7Hz, 3H) IR(cm -1 ) 3450, 3300, 2960, 1640, 1510, 1490, 1455, 1250, 885, 765 Example 175 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-3-methylpiperidine The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-methylpiperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.49-7.54(m, 1H), 7.16-7.24(m, 2H), 7.07-7.13(m, 1H), 6.83(s, 2H), 5.72(s, 1H), 5.09(s, 1H), 3.80-3.87(m, 1H), 3.46-3.54(m, 1H), 2.82(s, 4H), 2.70-2.82(m, 2H), 2.35-2.44(m, 1H), 1.76-1.84(m, 1H), 1.40-1.67(m, 3H), 1.38(s, 18H), 1.02-1.14(m, 1H), 0.88(t, J=6Hz, 3H) IR(cm -1 ) 3645, 3430, 3310, 2960, 2870, 1640, 1525, 1435, 1250, 1150, 750 Example 176 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-2-[2-(benzyloxy)ethyl]piperidine The title compound was prepared in a similar manner to that mentioned in Example 11, using 2-[2-(benzyloxy)ethyl]methylpiperidine instead of decylamine. m.p. 113-114°C 1 H-NMR(δ ppm, CDCl 3 ) 7.53(d, J=8Hz, 1H), 7.02-7.22(m, 8H), 6.89(s, 2H), 6.74(bs, 1H), 5.05(s, 1H), 4.35-4.44(m, 2H), 4.23-4.32(m, 1H), 4.03-4.15(m, 1H), 3.44-3.59(m, 2H), 2.63-2.77(m, 5H), 2.00-2.12(m, 1H), 1.44-1.82(m, 7H), 1.37(s, 18H) IR(cm -1 ) 3600, 3420, 2940, 2870, 1665, 1595, 1535, 1450, 1400, 1380, 1270, 1240, 1100, 765, 745 Example 177 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-3,3-dimethylpiperidine The title compound was prepared in a similar manner to that mentioned in Example 11, using 3,3-dimethylpiperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.54(dd, J=8, 1Hz, 1H), 7.16-7.23(m, 2H), 7.04-7.12(m, 1H), 6.84(s, 2H), 5.77(s, 1H), 5.08(s, 1H), 3.19(t, J=6Hz, 2H), 3.05(s, 2H), 2.82(s, 4H), 1.52-1.61(m, 2H), 1.33-1.43(m, 2H), 1.39(s, 18H), 0.92(s, 6H) IR(cm -1 ) 3645, 3430, 3320, 2960, 2870, 1640, 1520, 1440, 1250, 1165, 755 Example 178 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(4-fluorobenzyl)-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-fluoro-N-methylphenethylamine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.63(d, J=8Hz, 1H), 7.17-7.26(m, 4H), 7.11(dd, J=8, 7Hz, 1H), 6.97(dd, J=9, 9Hz, 2H), 6.75(s, 2H), 5.66(s, 1H), 5.06(s, 1H), 4.45(s, 2H), 2.73-2.84(m, 4H), 2.64(s, 3H), 1.33(s, 18H) IR(cm -1 ) 3645, 3430, 3320, 2965, 1650, 1515, 1440, 1380, 1300, 1230, 1160, 760 Example 179 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]-N'-(3,4-methylenedioxybenzyl)-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using 5-(methylaminomethyl)-1,3-dioxaindane instead of decylamine. m.p. 152-153°C 1 H-NMR(δ ppm, CDCl 3 ) 7.65(d, J=8Hz, 1H), 7.16-7.25(m, 2H), 7.10(dd, J=7, 7Hz, 1H), 6.76(s, 2H), 6.65-6.73(m, 2H), 5.92(s, 2H), 5.69(s, 1H), 5.06(s, 1H), 4.39(s, 2H), 2.72-2.83(m, 4H), 2.66(s, 3H), 1.34(s, 18H) Example 180 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-3-(benzyloxy)piperidine The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-benzyloxypiperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.44(d, J=8Hz, 1H), 7.22-7.34(m, 5H), 7.18(dd, J=7, 7Hz, 1H), 7.08(dd, J=7, 7Hz, 1H), 6.80(s, 2H), 5.82(s, 1H), 5.06(s, 1H), 4.47-4.56(m, 2H), 3.68-3.76(m, 1H), 3.43-3.51(m, 1H), 3.09-3.22(m, 3H), 2.71-2.83(m, 4H), 1.61-1.96(m, 3H), 1.38-1.50(m, 1H), 1.36(s, 18H) IR(cm -1 ) 3625, 3280, 2960, 1635, 1525, 1490, 1445, 1245, 1045, 940, 765 Example 181 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-2-(2-hydroxyethyl)piperidine The title compound was prepared in a similar manner to that mentioned in Example 11, using 2-(2-hydroxyethyl)piperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.46(d, J=8Hz, 1H), 7.16-7.24(m, 2H), 7.11(ddd, J=8, 7, 1Hz, 1H), 6.84(s, 2H), 6.00-6.21(br, 1H), 5.08(s, 1H), 4.51-4.62(m, 1H), 3.57-3.66(m, 1H), 3.48-3.18(m, 3H), 2.69-2.88(m, 5H), 1.40-2.03(m, 8H), 1.38(s, 18H) IR(cm -1 ) 3640, 3320, 2950, 2870, 1640, 1530, 1440, 1275, 1230, 1175, 755 Example 182 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-2-(2-acetoxyethyl)piperidine The title compound was prepared in a similar manner to that mentioned in Example 11, using 2-(2-acetoxyethyl)piperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.49(d, J=8Hz, 1H), 7.17-7.23(m, 2H), 7.09(d, J=7Hz, 1H), 6.84(s, 2H), 5.84(s, 1H), 5.08(s, 1H), 4.33-4.43(m, 1H), 4.00-4.16(m, 2H), 3.41-3.51(m, 1H), 2.76-2.90(m, 5H), 2.00-2.12(m, 1H), 1.97(s, 3H), 1.74-1.85(m, 1H), 1.38-1.72(m, 6H), 1.38(s, 18H) IR(cm -1 ) 3640, 3425, 2960, 2870, 1740, 1640, 1520, 1435, 1370, 1235, 750 Example 183 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-5-chlorophenyl]N'-(1-benzyl-4-piperidyl)urea The title compound was prepared in a similar manner to that mentioned in Example 108, using 4-(2-amino-4-chlorophenethyl)-2,6-di-tert-butylphenol instead of 4-(2-amino-3,5-difluorophenethyl)-2,6-di-tert-butylphenol. m.p. 155-156°C 1 H-NMR(δ ppm, CDCl 3 ) 7.41(s, 1H), 7.22-7.31(m, 5H), 7.08(s, 2H), 6.77(s, 2H), 5.22(s, 1H), 5.12(s, 1H), 4.20(d, J=8Hz, 1H), 3.45-3.65(m, 1H), 3.45(s, 2H), 2.75(s, 4H), 2.73-2.77(m, 2H), 2.04(t, J=11Hz, 2H), 1.85(d, J=11Hz, 2H), 1.38(s, 18H), 1.22-1.42(m, 2H) IR(cm -1 ) 3645, 3370, 1633, 1545, 1438, 1234, 699 Example 184 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-5-chlorophenyl]-N'-[2-(2-fluorophenyl)-2-methylpropyl]-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using 2-fluoro-β,β-dimethylphenethylamine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.53(d, J=8Hz, 1H), 7.17-7.28(m, 4H), 7.05-7.14(m, 2H), 6.94-7.03(m, 1H), 6.73(s, 2H), 5.49(s, 1H), 5.01(s, 1H), 3.70(s, 2H), 2.73-2.83(m, 4H), 2.21(s, 3H), 1.37(s, 6H), 1.29(s, 18H) IR(cm -1 ) 3640, 3430, 2965, 1660, 1510, 1490, 1440, 1210, 760 Example 185 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-5-chlorophenyl]-N'-methyl-N'-[1-(3,4-methylenedioxyphenyl)cyclopentyl]methylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using 5-[1-(N-methylaminomethyl)cyclopentyl]-1,3-dioxaindane instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.45(d, J=7Hz, 1H), 7.16-7.24(m, 2H), 7.06-7.13(m, 1H), 6.78(s, 1H), 6.72(s, 4H), 5.92(s, 2H), 5.32(s, 1H), 5.03(s, 1H), 3.42(s, 2H), 2.73-2.82(s, 4H), 2.02(s, 3H), 2.58-2.98(m, 8H), 1.30(s, 18H) IR(cm -1 ) 3640, 3430, 2960, 1660, 1510, 1490, 1435, 1235, 1450, 760 Example 186 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-5-chlorophenyl]-N'-(α-methylbenzyl)urea The title compound was prepared in a similar manner to that mentioned in Example 11, using α-methylbenzylamine instead of decylamine. m.p. 167-168°C 1 H-NMR(δ ppm, CDCl 3 ) 7.12-7.33(m, 9H), 6.77(s, 2H), 5.15(s, 1H), 5.09(s, 1H), 4.96(dq, J=7, 7Hz, 1H), 4.53(d, J=7Hz, 1H), 2.70-2.82(m, 4H), 1.40(d, J=7Hz, 3H), 1.37(s, 18H) IR(cm -1 ) 3625, 3320, 3275, 2960, 1630, 1565, 1435, 1235, 745, 700 Example 187 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-5-chlorophenyl]-N'-[2-(3,4-dichlorophenyl)-2-methylpropyl]-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using N-methyl-3,4-dichloro-β,β-dimethylphenethylamine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.48(d, J=8Hz, 1H), 7.43(d, J=2Hz, 1H), 7.37(d, J=10Hz, 1H), 7.17-7.27(m, 3H), 7.09-7.15(m, 1H), 6.71(s, 2H), 5.38(s, 1H), 5.08(s, 1H), 3.48(s, 2H), 2.72-2.84(m, 4H), 2.13(s, 3H), 1.36(s, 6H), 1.29(s, 18H) IR(cm -1 ) 3640, 3430, 3330, 2970, 1660, 1515, 1480, 1450, 1440, 1310, 1250, 1030, 880, 760 Example 188 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-5-chlorophenyl]-N'-[4-(4-fluorobenzyl)-3-morpholinyl]methylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-methylamino-4-(4-fluorobenzyl)morpholine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.19-7.37(m, 4H), 6.80-6.89(m, 4H), 6.76(s, 2H), 5.11(s, 1H), 5.05(s, 1H), 4.96(bs, 1H), 3.89(d, J=13Hz, 1H), 3.74(dd, J=12, 3Hz, 1H), 3.64(d, J=12Hz, 1H), 3.31-3.42(m, 4H), 3.03(d, J=13Hz, 1H), 2.70-2.88(m, 4H), 2.48-2.56(m, 1H), 2.45(d, J=12Hz, 1H), 2.10(dt, J=11, 3Hz, 1H), 1.37(s, 18H) Example 189 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-5-chlorophenyl]-N'-[2-(3,4-dichlorophenyl)-2-propyl]-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using 3,4-dichloroN,α,α-trimethylbenzylamine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.36-7.42(m, 2H), 7.24-7.29(m, 1H), 7.09-7.17(m, 3H), 7.02-7.07(m, 1H), 6.79(s, 2H), 5.52(s, 1H), 5.09(s, 1H), 2.81(s, 3H), 2.61-2.78(m, 4H), 1.63(s, 6H), 1.38(s, 18H) IR(cm -1 ) 3640, 3290, 2960, 2875, 1640, 1520, 1485, 1440, 1340, 1245, 1140, 1030, 755 Example 190 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-5-chlorophenyl]-N'-[2-(N-benzyl-N-ethylamino)ethyl]urea The title compound was prepared in a similar manner to that mentioned in Example 11, using N-benzyl-N-ethylethylenediamine instead of decylamine. m.p. 132-133°C 1 H-NMR(δ ppm, CDCl 3 ) 7.16-7.36(m, 7H), 6.92-6.98(m, 2H), 6.79(s, 2H), 5.12(bs, 1H), 5.09(s, 1H), 5.00-5.05(m, 1H), 3.43(s, 2H), 3.21(td, J=6, 5Hz, 2H), 2.74-2.90(m, 4H), 2.46(t, J=6Hz, 2H), 2.37(q, J=7Hz, 2H), 1.38(s, 18H), 0.87(t, J=7Hz, 3H) IR(cm -1 ) 3650, 3340, 3280, 2960, 2810, 1640, 1585, 1560, 1440, 1235, 1150, 865, 745, 705 Example 191 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)phenyl]carbamoyl]-3-ethoxycarbonylpiperidine The title compound was prepared in a similar manner to that mentioned in Example 11, using 3-ethoxycarbonylpiperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.53(d, J=8Hz, 1H), 7.15-7.22(m, 2H), 7.04-7.09(m, 1H), 6.84(s, 2H), 6.30(s, 1H), 5.07(s, 1H), 4.06-4.15(m, 2H), 3.74-3.81(m, 1H), 3.30-3.42(m, 2H), 3.10-3.17(m, 1H), 2.78-2.92(m, 4H), 2.52-2.59(m, 1H), 1.83-2.00(m, 2H), 1.46-1.66(m, 2H), 1.38(s, 18H), 1.22(t, J=7Hz, 3H) IR(cm -1 ) 3425, 2945, 2870, 1725, 1650, 1595, 1530, 1450, 1375, 1300, 1210, 1030, 885, 760 Example 192 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-5-chlorophenyl]-N'-(1-phenylcyclopentyl)-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using N-methyl-1-phenylcyclopentylamine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.47(d, J=8Hz, 1H), 7.33(dd, J=8, 1Hz, 1H), 7.08-7.18(m, 3H), 6.93-7.02(m, 3H), 6.78(s, 2H), 5.75(s, 1H), 5.07(s, 1H), 3.15(s, 3H), 2.57(t, J=8Hz, 2H), 2.23-2.39(m, 4H), 2.20(t, J=8Hz, 2H), 1.64-1.85(m, 4H), 1.42(s, 18H) IR(cm -1 ) 3630, 3410, 2950, 1640, 1520, 1440, 1345, 1230, 755, 700 Example 193 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-5-chlorophenyl]-N'-(1-benzyl-4-hydroxy-4-piperidyl)methylurea The title compound was prepared in a similar manner to that mentioned in Example 11, using 4-aminomethyl-1-benzyl-4-hydroxypiperidine instead of decylamine. 1 H-NMR(δ ppm, CDCl 3 ) 7.15-7.35(m, 9H), 6.76(s, 2H), 5.12(s, 1H), 5.08(bs, 1H), 4.56(t, J=5Hz, 1H), 3.51(s, 2H), 3.37(bs, 1H), 3.14(d, J=5Hz, 2H), 2.70-2.85(m, 4H), 2.50-2.60(m, 2H), 2.30-2.40(m, 2H), 1.45-1.60(m, 4H), 1.36(s, 18H) IR(cm -1 ) 3350, 2952, 1639, 1550, 1435, 1234, 741, 699 Example 194 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-cyclohexyl-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 108, using N-methylcyclohexylamine instead of 4-amino-1-benzylpiperidine. 1 H-NMR(δ ppm, CDCl 3 ) 6.70-6.80(m, 2H), 6.79(s, 2H), 5.09(s, 1H), 4.98(bs, 1H), 4.00-4.10(m, 1H), 2.75-2.90(m, 4H), 2.60(s, 3H), 1.60-1.80(m, 4H), 1.20-1.50(m, 24H) IR(cm -1 ) 3630, 3420, 2930, 1639, 1499, 1435, 1317, 1237, 1119 Example 195 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-[2-(3,4-dichlorophenyl)-2-methylpropyl]urea The title compound was prepared in a similar manner to that mentioned in Example 108, using 3,4-dichloro-β,β-dimethylphenethylamine instead of 4-amino-1-benzylpiperidine. m.p. 159-160°C 1 H-NMR(δ ppm, CDCl 3 ) 7.05-7.30(m, 3H), 6.65-6.78(m, 4H), 5.08-5.11(m, 1H), 4.27(bs, 1H), 3.72(bt, J=6Hz, 1H), 3.28-3.31(m, 2H), 2.65-2.80(m, 4H), 1.30-1.40(m, 18H), 1.20-1.30(m, 6H) IR(cm -1 ) 3640, 3310, 2958, 1638, 1566, 1436, 1235, 1118 Example 196 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-(1-adamantyl)urea The title compound was prepared in a similar manner to that mentioned in Example 108, using 1-adamantanamine instead of 4-amino-1-benzylpiperidine. m.p. 218-220°C 1 H-NMR(δ ppm, CDCl 3 ) 6.81(s, 2H), 6.70-6.80(m, 2H), 5.12(s, 1H), 4.60(bs, 1H), 3.93(bs, 1H), 2.88(t, J=7Hz, 2H), 2.78(t, J=7Hz, 2H), 2.03(bs, 3H), 1.91(d, J=3Hz, 6H), 1.64(bs, 6H), 1.40(s, 18H) IR(cm -1 ) 3642, 3375, 2910, 1650, 1562, 1495, 1436, 1235, 1120 Example 197 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-[2-(3,4-dichlorophenyl)-2-methylpropyl]-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 108, using N-methyl-3,4-dichloro-β,β-dimethylphenethylamine instead of 4-amino-1-benzylpiperidine. m.p. 145-147°C 1 H-NMR(δ ppm, CDCl 3 ) 7.15-7.40(m, 3H), 6.65-6.80(m, 4H), 5.04-5.06(m, 1H), 4.70-4.73(m, 1H), 3.46-3.49(m, 2H), 2.75-2.85(m, 4H), 2.20-2.24(m, 3H), 1.30-1.34(m, 24H) IR(cm -1 ) 3572, 3420, 2954, 1665, 1505, 1434, 1120 Example 198 (R)-N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-(α-ethoxycarbonylbenzyl)urea The title compound was prepared in a similar manner to that mentioned in Example 108, using (R)-α-phenylglycine ethyl ester instead of 4-amino-1-benzylpiperidine. m.p. 162-164°C 1 H-NMR(δ ppm, CDCl 3 ) 7.26-7.32(m, 5H), 6.73-6.80(m, 4H), 5.45(d, J=7Hz, 1H), 5.22(bd, J=7Hz, 1H), 5.12(s, 1H), 4.68(bs, 1H), 4.08-4.20(m, 2H), 2.72-2.89(m, 4H), 1.37(s, 18H), 1.18(t, J=7Hz, 3H) IR(cm -1 ) 3640, 3350, 2956, 1737, 1641, 1561, 1438, 1122 Example 199 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-[2-(3,4-dichlorophenyl)-2-propyl]urea The title compound was prepared in a similar manner to that mentioned in Example 108, using 3,4-dichloro-α,α-dimethylbenzylamine instead of 4-amino-1-benzylpiperidine. m.p. 224-226°C 1 H-NMR(δ ppm, CDCl 3 ) 7.42(d, J=2Hz, 1H), 7.31(d, J=9Hz, 1H), 7.18(dd, J=9, 2Hz, 1H), 6.75-6.80(m, 4H), 5.13(s, 1H), 4.62(bs, 1H), 4.53(bs, 1H), 2.56(t, J=7Hz, 2H), 2.77(t, J=7Hz, 2H), 1.57(s, 6H), 1.40(s, 18H) IR(cm -1 ) 3634, 3354, 2954, 1649, 1562, 1435, 1277, 1238, 1122 Example 200 1-[N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]carbamoyl]-4-benzylpiperidine The title compound was prepared in a similar manner to that mentioned in Example 108, using 4-benzylpiperidine instead of 4-amino-1-benzylpiperidine. 1 H-NMR(δ ppm, CDCl 3 ) 7.25-7.31(m, 2H), 7.20(t, J=7Hz, 1H), 7.12(d, J=7Hz, 2H), 6.71-6.80(m, 2H), 6.75(s, 2H), 5.09(s, 1H), 4.96(s, 1H), 3.73(bd, J=13Hz, 2H), 2.78-2.85(m, 4H), 2.67(t, J=12Hz, 2H), 2.53(d, J=7Hz, 2H), 1.58-1.71(m, 3H), 1.36(s, 18H), 1.12-1.22(m, 2H) IR(cm -1 ) 3636, 3418, 3026, 1627, 1499, 1435, 1235, 1120, 789, 748, 700 Example 201 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-[1-(4-dimethylaminophenyl)cyclopentyl]methylurea The title compound was prepared in a similar manner to that mentioned in Example 108, using 4-[(1-aminomethyl)-1-cyclopentyl]-N,N-dimethylaniline instead of 4-amino-1-benzylpiperidine. m.p. 165-166°C 1 H-NMR(δ ppm, CDCl 3 ) 6.92(d, J=9Hz, 2H), 6.75(s, 2H), 6.68-6.76(m, 2H), 6.54(d, J=9Hz, 2H), 5.08(s, 1H), 4.59(s, 1H), 3.82(bs, 1H), 3.19(d, J=6Hz, 2H), 2.89(s, 6H), 2.76(t, J=7Hz, 2H), 2.67(t, J=7Hz, 2H), 1.67-1.90(m, 8H), 1.37(s, 18H) IR(cm -1 ) 3674, 3250, 1615, 1520, 1435, 1233, 1121 Example 202 N-[2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-4,6-difluorophenyl]-N'-heptyl-N'-methylurea The title compound was prepared in a similar manner to that mentioned in Example 108, using N-methylheptylamine instead of 4-amino-1-benzylpiperidine. 1 H-NMR(δ ppm, CDCl 3 ) 6.70-6.80(m, 2H), 6.77(s, 2H), 5.10(s, 1H), 4.96(s, 1H), 3.21(t, J=8Hz, 2H), 2.75-2.86(m, 4H), 2.75(s, 3H), 1.42-1.56(m, 2H), 1.37(s, 18H), 1.20-1.35(m, 8H), 0.87(t, J=7Hz, 3H) IR(cm -1 ) 3640, 3300, 1638, 1503, 1435, 1236, 1120 The preparation of the compound of formula (II) used in each of the above examples is illustrated by the following reference examples. Reference Example 1 4-(2-Aminophenethyl)-2,6-di-tert-butylphenol (1) 2,6-di-tert-Butyl-4-(2-nitrostyryl)phenol To a solution of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (8.09 g, 34.5 mmol) and 2-nitrophenylacetic acid (9.40 g, 51.9 mmol) in xylene (60 ml) was added piperidine (0.3 ml) and the mixture was heated under reflux for 26 hrs while removing water producing with the progress of reaction. After allowing to stand overnight, hexane was added to afford as crystals 2,6-di-tert-butyl-4-(2-nitrostyryl)phenol (7.67 g, 62.9%). 1 H-NMR (δ ppm, CDCl 3 ) 7.94(dd, J=8, 1Hz, 1H), 7.76(d, J=8Hz, 1H), 7.57(dd, J=8, 8Hz, 1H), 7.44(d, J=16Hz, 1H), 7.33-7.37(m, 3H), 7.07(d, J=16Hz, 1H), 5.38(s, 1H), 1.48(s, 18H) (2) 4-(2-Aminophenethyl)-2,6-di-tert-butylphenol To a suspension of 2,6-di-tert-butyl-4-(2-nitrostyryl)phenol (16.4 g, 23.3 mmol) in ethanol (150 ml) was added a catalytic amount of 10% palladium carbon and the suspension was subjected to catalytic reduction at room temperature at 1-2.5 atms for 8 hrs and at 40°C for 3 hrs. After filtering the catalyst, distilling off the solvent gave 4-(2-aminophenethyl)-2,6-di-tert-butylphenol (15.1 g, 100%) as a viscous oil. 1 H-NMR (δ ppm, CDCl 3 ) 7.02-7.07(m, 2H), 6.94(s, 2H), 6.74-6.78(m, 1H), 6.67(d, J=8Hz, 1H), 5.06(s, 1H), 3.3-3.7(bs, 2H), 2.73-2.87(m, 4H), 1.41(s, 18H) Reference Example 2 (1) 2,6-Diisopropyl-4-(2-nitrostyryl)phenol To a solution of 3,5-diisopropyl-4-hydroxybenzaldehyde (0.95 g, 4.6 mmol) and 2-nitrophenyl acetic acid (1.1 g, 6.2 mmol) in xylene (10 ml) was added piperidine (0.05 ml) and the mixture was heated under reflux for 8 hrs while removing water producing with the progress of reaction. After distilling off the solvent followed by purification of the residue by a silica gel column chromatography, recrystallization from hexane gave 2,6-diisopropyl-4-(2-nitrostyryl)phenol (1.3 g, 87%) as crystals. 1 H-NMR (δ ppm, CDCl 3 ) 7.93-7.95(m, 1H), 7.75-7.77(m, 1H), 7.55-7.57(m, 1H), 7.45(d, J=16Hz, 1H), 7.34-7.38(m, 1H), 7.24(s, 2H), 7.07(d, J=16Hz, 1H), 4.95(s, 1H), 3.12-3.22(m, 2H), 1.32(s, 6H), 1.30(s, 6H) (2) 4-(2-Aminophenethyl)-2,6-diisopropylphenol To a suspension of 2,6-diisopropyl-4-(2-nitrostyryl)phenol (1.3 g, 4.0 mmol) in ethanol (20 ml) was added a catalytic amount of 10% palladium carbon and the suspension was subjected to catalytic reduction at 1-2.5 atms at room temperature for 7 hrs. After filtering the catalyst, distilling off the solvent gave 4-(2-aminophenethyl)-2,6-diisopropylphenol (1.0 g, 84%) as a viscous oil. 1 H-NMR (δ ppm, CDCl 3 ) 7.02-7.06(m, 2H), 6.83(s, 2H), 6.70-6.77(m, 1H), 6.65(d, J=7Hz, 1H), 4.67(s, 1H), 3.43(bs, 2H), 3.08-3.18(m, 2H), 2.73-2.87(m, 4H), 1.24(s, 6H), 1.22(s, 6H) Reference Example 3 4-(2-Aminostyryl)-2,6-di-tert-butylphenol To a solution of 2,6-di-tert-butyl-4-(2-nitrostyryl)phenol (1.1 g, 3.1 mmol) in methanol (15 ml) was added water (4 ml), conc. hydrochloric acid (0.2 ml) and iron powder (1.7 g, 30 mmol) and the mixture was heated under reflux for 5 hrs. After filtration, followed by extraction with ethyl acetate and water, the extract was washed with water, dried over MgSO 4 and concentrated. Purification of the residue by a silica gel column chromatography followed by recrystallization from hexane afforded 4-(2-aminostyryl)-2,6-di-tert-butylphenol (0.70 g, 70%). 1 H-NMR (δ ppm, CDCl 3 ) 7.36-7.38(m, 1H), 7.34(s, 2H), 7.06-7.10(m, 1H), 6.91-7.10(m, 2H), 6.78-6.82(m, 1H), 6.70-6.72(m, 1H), 5.29(s, 1H), 3.79(s, 2H), 1.47(s, 18H) Pharmacological Test 1. ACAT inhibitory activity The enzyme preparation, ACAT was prepared from liver microsme fractions of male rabbits according to the method of E. E. Largis et al. (Journal of Lipid Research, Vol. 30, pages 681-690, 1989). The activity was calculated by assaying the amount of the labelled cholesteryl esters formed from [1- 14 C]oleoyl-CoA and endogenous cholesterol according to the method of Kazuichi NATORI et al. (Japan J. Pharmacol., Vol. 42, pages 517-523, 1986). The result is shown in Table 1, in which percent inhibition of the formation of the labelled cholesteryl esters with a compound added at 10 -7 M is indicated as index for the ACAT inhibitory activity. The data reveals that the compounds of the invention have a superior ACAT inhibitory activity. 2. Antioxidative activity Human LDL was incubated in the presence of cupric sulfate (5 x 10 -6 M) and in the presence or absence of a compound (10 -5 M) for 5 hrs. After the incubation, the peroxidation of low-density lipoproteins (LDL) is evaluated by the formation of malondialdehyde (MDA), which is a sort of lipid peroxides according to the method of Simon J. T. Mao et al. (J. Med. Chem., Vol. 34, pages 298-302, 1991). Activity of the compound is shown by percent inhibition of the MDA formation as compared with control. The result is shown in Table 1. The data indicates that the compounds of the invention significantly lower the formation of the lipid peroxide (MDA). 3. Cholesterol-lowering activity Sprague-Dawley male rats were given a powdery feed containing 1% cholesterol and 0.5% cholic acid in an amount of 15 g per day per animal for 3 days to produce hypercholesteremic rats. Four days later, a compound suspended in 0.5% methylcellulose was administered orally at a dose of 30 mg/kg. Blood was drawn prior to and 5 hrs after the administration of the compound, for which the plasma cholesterol level was measured using a commercially available assay kit (Cholesterol E Test Wako, Wako Junyaku K.K.). The result is shown in Table 2. The data shows that the compounds of the invention significantly reduce blood cholesterol level. Compound of Example Percent Reduction of Cholesterol (%) 35 48.4 83 44.6 92 79.9 105 45.9 108 71.8 130 71.5 The pharmaceutical preparations comprising the compounds of the invention are prepared by conventional method in accordance with the following formulations. Tablets (per tablet) Compound of Example 6 50 mg Hydroxypropylcellulose 2 mg Corn starch 10 mg Lactose 100 mg Magnesium stearate 3 mg Talc 3 mg Capsules (per capsule) Compound of Example 17 200 mg Starch 8 mg Microcrystalline cellulose 23 mg Talc 8 mg Magnesium stearate 5 mg Granules (per divided packet) Compound of Example 41 1 mg Lactose 99 mg Corn starch 50 mg Crystalline cellulose 50 mg Hydroxypropylcellulose 10 mg Ethanol 9 mg

Claims: A compound of formula (I) or a pharmaceutically acceptable salt thereof in which: R 1 and R 2 , which may be the same or different, each represents a hydrogen atom, a halogen atom, a straight or branched (C 1 -C 6 )alkyl group or a straight or branched (C 1 -C 6 )alkoxy group, R 3 and R 4 , which may be the same or different, each represents a hydrogen atom, a straight or branched (C 1 -C 12 )alkyl group, a straight or branched (C 2 -C 20 )alkenyl group, a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxycarbonyl(C 1 -C 9 )alkyl group, a benzyloxycarbonyl(C 1 -C 6 )alkyl group in which the alkyl moiety is optionally substituted by phenyl, a N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkyl group, a N-(C 1 -C 6 )alkyl-N-benzylamino(C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkylthio(C 1 -C 6 )alkyl group, an oxo(C 1 -C 9 )alkyl group, a hydroxy(C 1 -C 6 )alkyl group, a dihydroxy(C 1 -C 6 )alkyl group, a cyclo(C 3 -C 15 )alkyl group, a cyclo(C 3 -C 8 )alkyl(C 1 -C 6 )alkyl group, a dicyclo(C 3 -C 9 )alkyl(C 1 -C 6 )alkyl group, a bicyclo(C 6 -C 9 )alkyl group, a tricyclo(C 9 -C 12 )alkyl group, in which in all cases the cycloalkyl group or the cycloalkyl moiety is optionally substituted by one or two substituents selected from the group consisting of (C 1 -C 6 )alkyl, hydroxy, amino, acetoxy, acetamido, phenyl, benzyloxy, dimethylaminophenyl, and methylenedioxyphenyl, which may be further fused with a benzene ring, an aryl group, an aryl(C 1 -C 6 )alkyl group, a diaryl(C 1 -C 6 )alkyl group, in which in all cases the aryl group or the aryl moiety is optionally substituted by one, two or three substituents selected from the group consisting of (C 1 -C 6 )alkyl, (C 1 -C 6 )alkyloxy, halogen, nitro, hydroxy, amino, dimethylamino, methylenedioxy, and pyrrolidinyl, a heterocyclic group or a heterocyclic group attached to a (C 1 -C 6 )alkylene chain, in which in all cases the heterocyclic group represents a saturated or unsaturated, 5 to 8 membered ring monocyclic or bicyclic, heterocyclic group containing 1 to 3 heteroatoms selected from the group consisting of S, O and N, and the heterocyclic group is optionally substituted by one or two substituents selected from the group consisting of acetyl, hydroxy, (C 1 -C 9 )alkyl, (C 1 -C 9 )alkyloxy, cyclo(C 3 -C 8 )alkyl, cyclo(C 3 -C 8 )alkyl(C 3 -C 10 )alkyl, pyridyl(C 1 -C 6 )alkyl, phenyl, phenyl(C 1 -C 6 )alkyl, diphenyl(C 1 -C 6 )alkyl, and phenylpiperazinyl, the phenyl group or the phenyl moiety being optionally substituted by one or two substituents selected from the group consisting of halogen, hydroxy, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, cyano, diethylamino and trifluoromethyl, which may be further fused with a benzene ring, and further R 3 and R 4 , together with the nitrogen atom to which they are attached, may form a saturated or unsaturated heterocyclic group, in which the heterocyclic group represents a 5 to 8 membered ring monocyclic or bicyclic, heterocyclic group or a group derived from a heterocyclic spiro compound, which may contain one or two heteroatoms selected from the group consisting of S, O or N, the heterocyclic group being optionally substituted by one or two substituents selected from the group consisting of (C 1 -C 6 )alkyl, hydroxy, hydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl, acetoxy(C 1 -C 6 )alkyl, (C 1 -C 9 )alkylcarbonyl, (C 1 -C 6 )alkoxycarbonyl, amino, tosyl, phenyl, halogenophenyl, (C 1 -C 6 )alkoxyphenyl, phenyl(C 1 -C 6 )alkyl, benzyloxy, benzyloxy(C 1 -C 6 )alkyl, tolyl, xylyl, benzoyl, methylenedioxyphenyl(C 1 -C 6 )alkyl, pyridyl, pyridylcarbonyl, piperidyl, pyrrolidinyl(C 1 -C 6 )alkyl and pyrrolidinylcarbonyl(C 1 -C 6 )alkyl, which may be further fused with a benzene ring, in which in all cases the alkyl and alkoxy moieties may be either straight or branched, with the proviso that both R 3 and R 4 do not represent a hydrogen atom at the same time; R 5 and R 6 , which may be the same or different, each represents a straight or branched (C 1 -C 6 )alkyl group; and the line represents -CH 2 CH 2 - or -CH=CH-. A compound of claim 1 wherein R 3 and R 4 , which may be the same or different, each represents a hydrogen atom, a straight or branched (C 1 -C 10 )alkyl group, a straight or branched (C 3 -C 17 )alkenyl group, a (C 1 -C 4 )alkoxy(C 1 -C 4 )alkyl group, a (C 1 -C 4 )alkoxycarbonyl(C 1 -C 4 )alkyl group, a benzyloxycarbonyl(C 1 -C 4 )alkyl group in which the alkyl moiety is optionally substituted by phenyl, a (C 1 -C 4 )alkylthio(C 1 -C 4 )alkyl group, a cyclo(C 3 -C 12 )alkyl group or a cyclo(C 5 -C 7 )alkyl(C 1 -C 4 )alkyl group in which the cycloalkyl group or the cycloalkyl moiety is optionally monosubstituted by a substituent selected from the group consisting of (C 1 -C 4 )alkyl, hydroxy, amino, acetoxy, acetamide, phenyl, benzyloxy, dimethylaminophenyl and methylenedioxyphenyl, or the cycloalkyl group or the cycloalkyl moiety is optionally fused with a benzene ring; a dicyclohexyl(C 1 -C 4 )alkyl group, a bicyclooctyl group, an adamantyl group, a phenyl group optionally substituted by (C 1 -C 4 )alkyl or hexyloxy, a naphthyl group, an anthryl group, a phenyl(C 1 -C 4 )alkyl group in which the phenyl moiety is optionally substituted by one or two substituents selected from the group consisting of (C 1 -C 4 )alkyl, (C 1 -C 4 )alkyloxy, halogen, nitro, hydroxy, amino, dimethylamino, methylenedioxy and pyrrolidinyl; a diphenyl(C 1 -C 4 )alkyl group, a heterocyclic group or a heterocyclic group attached to a (C 1 -C 4 )alkylene chain in which the heterocyclic group represents a saturated or unsaturated, 5 or 6 membered ring monocyclic or bicyclic, heterocyclic group containing 1 or 2 nitrogen atoms and the heterocyclic group is optionally substituted by one or two substituents selected from the group consisting of acetyl, hydroxy, (C 1 -C 6 )alkyl, cyclohexyl, pyridyl(C 1 -C 4 )alkyl, phenyl(C 1 -C 4 )alkyl or diphenyl(C 1 -C 4 )alkyl in which the phenyl moiety is optionally substituted by one or two substituents selected from the group consisting of halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, cyano, diethylamino and trifluoromethyl, and phenylpiperazinyl, which may be further fused with a benzene ring; and further R 3 and R 4 , together with the nitrogen atom to which they are attached may form a saturated or unsaturated heterocyclic ring, in which the heterocyclic group represents a 5 to 7 membered ring monocyclic or bicyclic, heterocyclic group or a group derived from a heterocyclic spiro compound, which contain one or two nitrogen atoms, the heterocyclic group being optionally substituted by one or two substituents selected from the group consisting of (C 1 -C 4 )alkyl, hydroxy(C 1 -C 4 )alkyl, acetoxy(C 1 -C 4 )alkyl, (C 1 -C 6 )alkylcarbonyl, (C 1 -C 4 )alkoxycarbonyl, tosyl, phenyl, phenyl(C 1 -C 4 )alkyl, benzyloxy, benzyloxy(C 1 -C 4 )alkyl, benzoyl, methylenedioxyphenyl(C 1 -C 4 )alkyl, pyridylcarbonyl, piperidyl and pyrrolidinylcarbonyl(C 1 -C 4 )alkyl. A compound of claim 2 wherein R 3 and R 4 , which may be the same or different, each represents a hydrogen atom, a straight or branched (C 1 -C 7 )alkyl group, a cyclo(C 4 -C 8 )alkyl group, a heterocyclic group or a heterocyclic group attached to a (C 1 -C 4 )alkylene chain in which the heterocyclic group represents a saturated or unsaturated, 5 or 6 membered ring monocyclic or bicyclic, heterocyclic group containing one nitrogen atom and the heterocyclic group is optionally substituted by one or two substituents selected from the group consisting of methyl, ethyl, cyclohexyl, pyridylmethyl, and phenyl(C 1 -C 3 )alkyl in which the phenyl moiety being optionally substituted by one or two substituents selected from the group consisting of halogen, methoxy, cyano, dimethylamino and trifluoromethyl, which may be further fused with a benzene ring. A compound of claim 3 wherein R 3 and R 4 , which may be the same or different, each represents a hydrogen atom, a straight or branched (C 1 -C 4 )alkyl group, cyclohexyl, cycloheptyl, pyrrolidinyl or piperidyl, the latter two heterocyclic groups being optionally substituted by one or two substituents selected from the group consisting of methyl, ethyl, cyclohexyl, pyridylmethyl, and phenyl(C 1 -C 3 )alkyl in which the phenyl moiety being optionally substituted by one or two substituents selected from the group consisting of halogen, methoxy, cyano, diethylamino and trifluoromethyl, which may be further fused with a benzene ring. A compound of claim 2 wherein R 3 and R 4 , together with the nitrogen atom to which they are attached, may form a saturated or unsaturated heterocyclic ring, in which the heterocyclic group represents a 5 or 6 membered ring monocyclic or bicyclic, heterocyclic group which contain one or two nitrogen atoms, the heterocyclic group being optionally substituted by one or two substituents selected from the group consisting of methyl, hydroxyethyl, acetoxyethyl, pentylcarbonyl, ethoxycarbonyl, tosyl, phenyl, benzyl, benzyloxy, benzyloxyethyl, benzoyl, methylenedioxybenzyl, pyridylcarbonyl and piperidyl, which may be further fused with a benzene ring. A compound of formula (I) or a pharmaceutically acceptable salt thereof as claimed in any of claims 1 to 5 for use in therapy. A compound as claimed in claim 6 for use in ACAT inhibition. A pharmaceutical composition comprising as an active ingredient a compound of formula (I) or a pharmaceutically acceptable salt thereof as claimed in any of claims 1 to 5 and a pharmaceutically acceptable carrier and/or excipient. Use of a compound of formula (I) or a pharmaceutically acceptable salt thereof as claimed in any of claims 1 to 5 in the manufacture of a medicament for the prophylaxis and treatment of hypercholesterolemia and atherosclerosis.

Inventors: HIRAMOTO SHIGERU, HORIGOME MASATO, KATSUYAMA KOICHI, KINOSHITA NOBUHIRO, MIURA KATSUTOSHI, NAKATA FUMIHISA, OSHIDA NORIO, SUEDA NORIYOSHI, TSUKADA YOKO, YAMADA KAZUHIKO, YANAI MAKOTO, HIRAMOTO, SHIGERU, HORIGOME, MASATO, KATSUYAMA, KOICHI, KINOSHITA, NOBUHIRO, MIURA, KATSUTOSHI, NAKATA, FUMIHISA, OSHIDA, NORIO, SUEDA, NORIYOSHI, TSUKADA, YOKO, YAMADA, KAZUHIKO, YANAI, MAKOTO, HIRAMOTO, SHIGERU, C/O NISSHIN FLOUR MILLING CO., HORIGOME, MASATO, C/O NISSHIN FLOUR MILLING CO., KATSUYAMA, KOICHI, C/O NISSHIN FLOUR MILLING CO., KINOSHITA, NOBUHIRO, C/O NISSHIN FLOUR MILLING CO., MIURA, KATSUTOSHI, C/O NISSHIN FLOUR MILLING CO., NAKATA, FUMIHISA, C/O NISSHIN FLOUR MILLING CO., OSHIDA, NORIO, C/O NISSHIN FLOUR MILLING CO., SUEDA, NORIYOSHI, C/O NISSHIN FLOUR MILLING CO., TSUKADA, YOKO, C/O NISSHIN FLOUR MILLING CO., YAMADA, KAZUHIKO, C/O NISSHIN FLOUR MILLING CO., YANAI, MAKOTO, C/O NISSHIN FLOUR MILLING CO.
Applicants: NISSHIN FLOUR MILLING CO, NISSHIN FLOUR MILLING CO., LTD.
Application year: 1994
Main classification: C07C275
IPC codes: C07D295, C07D211, C07D521, C07D498, C07D401, C07C275, C07D451, C07D217, C07D209, C07D215, C07D265, C07D207, C07D471, C07D317, C07D491, C07D333, C07D213, C07D249, C07D453, C07C323, C07D307